Herbicidal acetylenic pyrimidines and triazines

ABSTRACT

Sulfonylureas derived from acetylenic pyrimidines and triazines, useful as pre- and postemergence herbicides. Typical of this group is 2-[[(4-ethynyl-6-methylpyrimidine-2-yl)aminocarbonyl]-aminosulfonyl]-benzoic acid, methyl ester.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a continuation-in-part of copending applicationbearing U.S. Ser. No. 638,962, filed on Aug. 8, 1984, abandoned.

BACKGROUND OF THE INVENTION

U.S. Pat. Nos. 4,127,405 and 4,169,719 disclose herbicidalbenzenesulfonylureas.

No. EP-A-9,419 discloses herbicidal sulfonamides of formula ##STR1##where R is ##STR2## R₄ is Cl, Br, F, NO₂, CH₃, OCH₃, CF₃ or S(O)_(n) R₃;

R₅ is C₁ -C₆ alkyl or C₃ -C₄ alkenyl;

n is 0, 1 or 2;

X is CH₃ or OCH₃ ;

Z is CH or N; and

Y is, among other values, C₂ -C₄ alkynyl.

U.S. Pat. No. 4,383,113 discloses herbicidal benzenesulfonamides offormula ##STR3## where R can be, among other values, C₁ -C₁₂ alkyl, C₃-C₁₀ alkenyl or C₂ -C₆ alkyl substituted with one to four substituentsselected from 0-3 atoms of F, Cl or Br, 0-2 methoxy groups and 0-1 cyanogroups;

X is H, Cl, CH₃, OCH₃, OCH₂ CH₃ or OCH₂ CH₂ OCH₃ ; and

Y is, among other values, CH₂ C.tbd.CR₁₃ where R₁₃ is H, CH₃ or CH₂ Cl.

U.S. Pat. No. 4,421,550 discloses herbicidal sulfonamides of formula##STR4## where R₁ can be, among other values, C₃ -C₄ alkynyl;

R₂ can be, among other values, C₁ -C₄ alkyl or C₁ -C₄ alkyl substitutedwith 1-3 F atoms; and

Z can be, among other values, optionally substituted phenyl, benzyl,1-naphthyl, 3-pyridyl or 2- or 3-thienyl.

SUMMARY OF THE INVENTION

This invention relates to compounds of Formula I, agriculturallysuitable compositions containing them, and use of these compounds andcompositions as preemergent and/or postemergent herbicides or plantgrowth regulants. ##STR5## wherein W₁ is O or S;

R is H or CH₃ ;

L is ##STR6## R₁ is OCH₂ CH₂ OCH₃, CO₂ R₁₇, SO₂ NR₁₈ R₁₉, SO₂N(OCH₃)CH₃, OSO₂ R₂₀, WCF₃, WCHF₂, C₃ -C₄ alkenyloxy, C₃ -C₄ alkynyloxy,C₁ -C₂ alkyl substituted with OCH₃ or OCH₂ CH₃, C₆ H₅, C₃ -C₄ alkynyl,CH═CHCF₃, CH═CHBr, or Q;

Q is ##STR7## R₂ is H, F, Cl, Br, CF₃, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, C₁-C₂ alkylthio, C₂ -C₃ alkoxyalkyl, C₂ -C₃ alkylthioalkyl or OCF₂ H;

R₃ is H, CH₃, OCH₃, F, Cl, Br, SO₂ N(CH₃)₂, OSO₂ CH₃ or S(O)_(n) CH₃ ;

R₄ is CH₃, CH₂ CH₃, OCH₃, OCH₂ CH₃, F, Cl, Br, SO₂ NR₁₈ R₁₉, SO₂N(OCH₃)CH₃, S(O)_(n) R₂₁, C₃ -C₄ alkenyloxy, CH₂ OCH₃ or CH₂ OCH₂ CH₃ ;

R₅ is C₁ -C₃ alkyl, F, Cl, Br, NO₂, CO₂ R₁₇, SO₂ NR₁₈ R₁₉, SO₂N(OCH₃)CH₃ or S(O)_(n) R₂₁ ;

R₆ is Cl, NO₂, CO₂ CH₃, CO₂ CH₂ CH₃, SO₂ N(CH₃)₂, OSO₂ CH₃, SO₂ CH₃, SO₂CH₂ CH₃, OCH₃ or OCH₂ CH₃ ;

R₇ is H, CH₃ or CH₂ CH₃ ;

R₈ is H, CH₃ or CH₂ CH₃ ;

R₉ is H or CH₃ ;

R₁₀ is H or CH₃ ;

R₁₁ is H or CH₃ ;

R₁₂ is H, C₁ -C₅ alkyl, C₂ -C₃ alkoxycarbonyl, C₂ -C₃ alkylcarbonyl, C₁-C₃ alkyl substituted by 1-3 halogens selected from 0-3 F, 0-3 Cl or 0-1Br, C₂ -C₄ alkyl substituted by OCH₃, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl orbenzyl;

R₁₃ is H or C₁ -C₃ alkyl;

R₁₄ is H or CH₃ ;

R₁₅ is C₁ -C₃ alkyl, F, Cl, Br, NO₂, CO₂ R₁₇, SO₂ NR₁₈ R₁₉, SO₂ R₂₁ orOCF₂ H;

R₁₆ is H, CO₂ CH₃, CO₂ CH₂ CH₃, SO₂ CH₃ or SO₂ CH₂ CH₃ ;

R₁₇ is C₁ -C₄ alkyl, CH₂ CH₂ OCH₃, CH₂ CH₂ Cl or CH₂ CH═CH₂ ;

R₁₈ is H or C₁ -C₃ alkyl;

R₁₉ is C₁ -C₃ alkyl;

R₂₀ is C₁ -C₃ alkyl or N(CH₃)₂ ;

R₂₁ is C₁ -C₃ alkyl or CH₂ CH═CH₂ ;

R₂₂ is H or C₁ -C₃ alkyl;

R₂₃ is H or Cl;

R₂₄ is H or Cl;

R₂₅ is H or CH₃ ;

m is 0 or 1;

n is 0 or 2;

Q₁ is O, S, SO₂ or NR₁₄ ;

Q₂ is O or S;

Q₃ is S or NR₂₂ ;

W is O, S or SO₂ ;

A is ##STR8## X is H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkyl, C₁-C₃ haloalkoxy, C₂ -C₄ alkoxyalkoxy, C₁ -C₃ alkylamino, di(C₁ -C₂alkyl)amino, amino or cyclopropyl;

Y is H, C₁ -C₅ alkyl, Br, I, phenyl optionally substituted with CH₃,OCH₃, halogen, NO₂, CF₃ or SCH₃, or C₁ -C₃ alkyl substituted with OH,OCH₃, OC₂ H₅ or F;

Z is CH or N;

X₁ is H or CH₃ ;

Y₁ is O or CH₂ ;

X₂ is CH₃, CH₂ CH₃ or CH₂ CF₃ ; and

Y₂ is H or CH₃ ;

and their agriculturally suitable salts;

provided that

(1) the total number of carbon atoms of R₁₈ and R₁₉ is less than orequal to four;

(2) when m is 1, then R₉ is H;

(3) when L is L-17, then R₁₃ and R₁₄ are not simultaneously H;

(4) when L is L-18, then R₁₅ is adjacent to the sulfonylurea bridge SO₂NHC(W₁)N(R)A;

(5) when L is L-8 and Q₁ is NR₁₄, then m is 1;

(6) when A is A-5 and L is L-1, L-2, L-3, L4, L-5, L-6 or L-7, then X₁is H;

(7) when the total number of carbon atoms of X and Y is greater thanfour, then the combined number of carbons of the substituents on L isless than or equal to four; and

(8) when L is L-8, L-9, L-11, L-12 or L-17 and R₂ is C₂ -C₃ alkoxyalkylor C₂ -C₃ alkylthioalkyl, then Y is other than H or C₁ -C₂ alkyl.

In the above definitions, the term "alkyl" used either alone or incompound words such as "alkylthio" or "haloalkyl", denotes straightchain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl andthe different butyl or pentyl isomers.

Alkoxy denotes methoxy, ethoxy, n-propoxy and isopropoxy.

Alkenyl denotes straight chain or branched alkenes, e.g., 1-propenyl,2-propenyl, 3-propenyl and the different butenyl isomers.

Alkynyl denotes straight chain or branched alkynes, e.g., ethynyl,1-propynyl, 2-propynyl and the different butynyl isomers.

Alkylcarbonyl denotes acetyl or propionyl, and the term alkylamino isdefined in an analogous manner.

The term "halogen", either alone or in compound words such as"haloalkyl", denotes fluorine, chlorine, bromine or iodine.

In terms such as C₂ -C₃ alkylthioalkyl, the specified number of carbonatoms is meant to define the total number of carbon atoms in thatsubstituent group. For example, C₂ -C₃ alkylthioalkyl would designateCH₂ SCH₃, CH₂ SC₂ H₅, CH₂ CH₂ SCH₃ or CH(CH₃)SCH₃.

Preferred for reasons of their higher herbicidal activity and/or morefavorable ease of synthesis are:

(1) Compounds of Formula I where R is H, W₁ is O and A is A-1, A-2, A-3or A-4;

(2) Compound of Preferred Group 1 where Y is H or C₁ -C₃ alkyl;

(3) Compounds of Preferred Group 2 where L is L-1, L-2, L-3, L-4, L-5,L-6, L-8, L-9, L-10, L-11, L-12, L-13, L-17 or L-18, Q₁ is O, S or SO₂and X is CH₃, CH₂ CH₃, OCH₃, OCH₂ CH₃, CH₂ OCH₃, CH₂ OCH₂ CH₃, OCH₂ CF₃,OCH₂ CF₂ H, OCH₂ CH₂ F or OCF₂ H;

(4) Compounds of Preferred Group 3 where R₁ is CO₂ R₁₇, SO₂ NR₁₈ R₁₉,SO₂ N(OCH₃)CH₃, WCF₃, WCHF₂, ##STR9## R₂ is H, F, Cl, CH₃, OCH₃ or SCH₃; R₃ is CH₃, OCH₃, Cl, Br, OSO₂ CH₃ or S(O)_(n) CH₃ ;

R₄ is CH₃, OCH₃, Cl, SO₂ N(CH₃)₂, SO₂ CH₃ or SO₂ CH₂ CH₃ ;

R₅ is CH₃, Cl, NO₂, CO₂ R₁₇, SO₂ N(CH₃)₂, SO₂ CH₃ or SO₂ CH₂ CH₃ ;

R₇ is H or CH₃ ;

R₈ is H or CH₃ ;

R₉ is H;

R₁₁ is H;

R₁₂ is H, C₁ -C₄ alkyl, CH₂ CH₂ OCH₃ or CH₂ CH═CH₂ ;

R₁₃ is H or CH₃ ;

R₁₅ is CH₃, CH₂ CH₃, Cl, NO₂, CO₂ CH₃, CO₂ CH₂ CH₃, Br, SO₂ N(CH₃)₂, SO₂CH₃, SO₂ CH₂ CH₃ or OCF₂ H;

R₁₈ is H or CH₃ ;

R₁₉ is C₁ -C₂ alkyl; and

W is O or S;

(5) Compounds of Preferred Group 4 where A is A-1, X is CH₃, CH₂ CH₃,OCH₃ or OCH₂ CH₃ and Y is H or CH₃ ;

(6) Compounds of Preferred Group 5 where L is L-1 and R₁ is CO₂ CH₃, CO₂CH₂ CH₃, SO₂ N(CH₃)₂, or OCF₂ H;

(7) Compounds of Preferred Group 5 where L is L-2;

(8) Compounds of Preferred Group 5 where L is L-4;

(9) Compounds of Preferred Group 5 where L is L-5;

(10) Compounds of Preferred Group 5 where L is L-8;

(11) Compounds of Preferred Group 5 where L is L-9;

(12) Compounds of Preferred Group 5 where L is L-10;

(13) Compounds of Preferred Group 5 where L is L-11;

(14) Compounds of Preferred Group 5 where L is L-12;

(15) Compounds of Preferred Group 5 where L is L-13;

(16) Compounds of Preferred Group 5 where L is L-17; and

(17) Compounds of Preferred Group 5 where L is L-18.

Especially preferred for reason of highest herbicidal efficacy and/orgreatest ease of synthesis are:

(i)2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoicacid, methyl ester, m.p. 185° to 190° C.;

(ii)2-[[(4-ethynyl-6-methoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoicacid, methyl ester, m.p. 158° to 161° C.(d); and

(iii)N'-[(4-ethynyl-6-methoxy-1,3,5-triazin-2-yl)aminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide,m.p. 135° to 139° C.(d).

DETAILS OF THE INVENTION Synthesis

The compounds of Formula I can be prepared by one or more of the methodsdescribed below in Equations 1, 2, 3, and 4.

As shown in Equation 1, compounds of Formula I where L is other thanL-20 can be prepared by reacting a sulfonyl isocyanate of Formula IIwith an appropriate heterocyclic amine of Formula III. ##STR10##

The reaction is carried out at 25° to 100° C. in an inert, aproticsolvent such as methylene chloride or xylene for 0.5 to 24 hours astaught in U.S. Pat. No. 4,127,405.

Compounds of Formula I, where R₁, R₅ and R₆ of the structures designatedL are other than CO₂ R₁₇, and L is not L₁₁, L₁₂, L₁₅ or L₁₇, can beprepared by reacting the sulfonamides of Formula IV with an appropriatemethyl carbamate of Formula V in the presence of at least an equimolaramount of trimethylaluminum, as shown in Equation 2. ##STR11##

The reaction is carried out at 25° to 40° C. in a solvent such asmethylene chloride for 10 to 96 hours under an inert atmosphere astaught in EPO No. 84,244 (published July 27, 1983). The requiredcarbamates V are prepared by reacting the corresponding amines III withdimethylcarbonate or methyl chloroformate in the presence of a strongbase.

Alternatively, compounds of Formula I can be prepared by reacting asulfonylcarbamate of Formula VI with an appropriate amine of FormulaIII, as shown in Equation 3. ##STR12##

The reaction is carried out at 50° to 100° C. in a solvent such asdioxane for 0.5 to 24 hours as taught in EPO publication No. 44807. Therequired carbamates VI are prepared by reacting the correspondingsulfonamides IV with diphenylcarbonate in the presence of a strong base.

Additionally, compounds of Formula I can be prepared by reacting asulfonamide of Formula IV with an appropriate heterocyclic phenylcarbamate of Formula VII in the presence of a nonnucleophilic base suchas 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as shown below in Equation4. ##STR13##

The reaction is carried out at 20° to 100° C. in an inert solvent, suchas dioxane, for 0.5 to 24 hours by the methods taught in EPO publicationNo. 44807. The required carbamates, VII, are prepared by reacting thecorresponding heterocyclic amines, III, with phenylchloroformate in thepresence of a base.

The intermediate sulfonyl isocyanates of Formula II in Equation 1 can beprepared as shown in Equations 5 and 6.

As shown in Equation 5, sulfonyl isocyanates of Formula II can beprepared by the reaction of sulfonamides of Formula IV with phosgene inthe presence of n-butyl isocyanate and a tertiary amine catalyst, suchas 1,4-diazabicyclo-[2.2.2]octane (DABCO), at reflux in a solvent suchas xylene by the method of U.S. Pat. No. 4,238,621. ##STR14##

The sulfonyl isocyanates can also be prepared from the sulfonamides by atwo step procedure involving (a) reacting the sulfonamides with n-butylisocyanate in the presence of a base such as K₂ CO₃ at reflux in aninert solvent such as 2-butanone forming a n-butyl sulfonylurea; and (b)reacting this compound with phosgene and a tertiary amine catalyst atreflux in xylene solvent. The method is similar to a procedure taught byUlrich and Sayigh, Newer Methods of Preparative Organic Chemistry, Vol.VI, p. 223-241, Academic Press, New York and London, W. Foerst Ed.

Alternatively, as shown in Equation 6, the sulfonyl isocyanates ofFormula II can be prepared by reacting the corresponding sulfonylchlorides VIII with cyanic acid salts. ##STR15##

The reaction is carried out at 25° to 100° C. in an inert aproticsolvent such as acetonitrile for 0.5-24 hours in the presence ofphosphorous pentoxide and an alkali metal salt such as lithium iodide,according to the teachings of Japanese Pat. No. 76/26,816 (Chem. Abst.,85:77892e (1976)).

Sulfonyl isothiocyanates of Formula II, where W₁ is S, can be preparedaccording to the methods taught by K. Hartke, Arch. Pharm., 299, 174(1966).

As shown in Equation 7, sulfonamides of Formula IV can be prepared fromthe corresponding sulfonyl chlorides of Formula VIII by contacting witheither anhydrous or aqueous ammonia. ##STR16##

The preparation of sulfonamides from sulfonyl chlorides is widelyreported in the literature, for reviews see: Hawking et al., "TheSulfonamides," H. K. Lewis and Co., London, 1950 and Northey, "TheSulfonamides and Allied Compounds," Reinhold Publishing Corp., New York,1948.

The requisite sulfonyl chlorides of Formula VIII can be synthesized byknown methods or with slight modifications thereof, by one skilled inthe art. Several representative teachings are listed below. Sulfonylchlorides, where L is L-1 are described generally in U.S. Pat. No.4,127,405 and more specifically for o-esters in U.S. Pat. No. 4,394,506;o-sulfonamides in U.S. Pat. No. 4,310,346; o-fluoro-substituted-methylsand -methoxys in No. EP-A-23,422; o-heterocycles in No. EP-A-83,975 andNo. EP-A-85,476; and o-sulfonates in U.S. Pat. No. 4,435,205.Additionally, sulfonyl chlorides of Formula VIII can be made accordingto the teachings in U.S. Pat. No. 4,370,479, No. EP-A-13,480, No.EP-A-64,804, No. EP-A-30,142 and U.S. Pat. No. 4,398,939, U.S. Pat. No.4,420,325, No. EP-A-107,979 and No. EP-A-95,925 for L₂, L₃, L₄ to L₆,L₇, L₈ to L₁₇ and L₁₈ to L₁₉.

Heterocycles of Formula III can be synthesized by the route shown inEquation 8a and 8b; where J is Cl, Br or I; L' is a neutral ligand suchas triphenyl phosphine; P is C(CH₃)₂ OH or SiMe₃ ; T is U where J is--C.tbd.C--P and ##STR17## wherein R₂₆ is Y, but not H, Br or I.

The reaction is carried out at 20° to 100° C. for 0.5 to 48 hours bymixing the haloheterocycle of Formula IX with a terminal acetylene ofFormula X or XII (one or more equivalents), copper (I) halide (0.005 to0.1 equivalents), palladium catalyst (0.005 to 0.1 equivalents), analkylamine solvent such as diethylamine or an inert solvent such asdichloromethane or tetrahydrofuran (THF) plus a tertiary amine (2 to 100equivalents) such as triethylamine. However, when Z is N only the secondsolvent system is used. The palladium coupling of terminal acetylenes toaromatic halides is well known in the literature. Methods similar to theabove reactions are taught by K. Edo, T. Sakamoto and H. Yamanaka inChem. Pharm. Bull., 26 (1978), 3843-3850.

P is a protecting group which can be removed by methods known in theliterature. When P is a 2-hydroxy-2-propyl moiety, removal of it to theethyne is effected with an alkali hydroxide in an inert solvent such astoluene at 20° to 130° C. for 0.5 to 24 hours. A similar procedure istaught by D. Ames, D. Bull and C. Takundwa in Synthesis, 1981, 364-365.

When P is a trimethylsilyl moiety, it can be removed by mixing thetrimethylsilyl protected acetylene in methanol with dilute alkalihydroxide at 0° to 80° C. for 0.5 to 25 hours. The method is similar tothat taught by S. Takahasi, Y. Kuroyama, K. Sonogashira and N. Hagiharain Synthesis, 1980, 627-630.

The requisite haloheterocycles of Formula IX where R is H or CH₃ areeither known or can be prepared by methods known to those skilled in theart.

Additionally, alkynyl triazines may be prepared by the route shown inEquation 9. A procedure is described in U.S. Pat. No. 3,778,441.##STR18## where R' is C₁ to C₃ alkyl or CH₂ CH₂ OCH₃.

Derivatization of terminal acetylenes is well known in the literature.Several general transformations are shown below in Equation 10.##STR19##

Literature examples may be found in Yamaguchi, et. al., Tet. Let. 24(1983), 391 to 394; Suzuki, et. al., J. Am. Chem. Soc., 95, 3080 (1973);and Hofmeister, et al., Angew Chem. Int. Ed. Engl., 23 (1984), 727 to729; for Equations 10a, b, and c, respectively.

For a review of the synthesis and reactions of 2-aminopyrimidines (III,U is U-1 and Z=CH) see The Chemistry of Heterocyclic Compounds, Vol. 16,John Wiley and Sons, New York (1962). For a review of the synthesis andreactions of 2-amino-s-triazines (III, U is U-1 and Z=N) see TheChemistry of Heterocyclic Compounds, Vol 13, John Wiley, New York(1959), F. C. Schaefer, U.S. Pat. No. 3,154,547 and F. C. Schaefer andK. R. Huffman, J. Org. Chem., 28, 1812 (1963). Also, a method for thesynthesis of 2-ethynyl-4-amino-6-methoxy-s-triazine is taught in U.S.Pat. No. 3,778,441.

The synthesis of bicyclic amines where U is U-2 or U-3 is taught in U.S.Pat. No. 4,339,267. The synthesis of bicyclic amines where U is U-4 istaught in No. EP-A-46,677. The synthesis of triazoles where U is U-5 istaught in U.S. Pat. No. 4,421,550.

Additionally, heterocyclic amines where A is A-1 and Z is N are eitherknown or can be prepared by methods taught in Ger. Offen. No. 2,209,470.

Heterocycles of Formula III where R is CH₃ may be prepared by thereaction sequence shown in Equation 8. When Z is N, these compounds mayoften be more conveniently synthesized by reaction of the correspondingcompound of formula A-Cl with methylamine by procedures similar to thosedisclosed in Ger. Offen. No. 2,209,470 for analogous reactions withammonia.

Agriculturally suitable salts of compounds of Formula I are also usefulherbicides and can be prepared in a number of ways known to the art. Forexample, metal salts can be made by contacting compounds of Formula Iwith a solution of an alkali or alkaline earth metal salt have asufficiently basic anion (e.g., hydroxide, alkoxide, carbonate orhydride). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of onecation for another. Cationic exchange can be effected by directcontacting of an aqueous solution of a salt of a compound of Formula I(e.g., alkali metal or quaternary amine salt) with a solution containingthe cation to be exchanged. This method is most effective when thedesired salt containing the exchanged cation is insoluble in water,e.g., a copper salt, and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a saltof a compound of Formula I (e.g., an alkali metal or quaternary aminesalt) through a column packed with a cation exchange resin containingthe cation to be exchanged. In this method, the cation of the resin isexchanged for that of the original salt and the desired product iseluted from the column. This method is particularly useful when thedesired salt is water-soluble, e.g., a potassium, sodium, or calciumsalt.

Acid addition salts, useful in this invention, can be obtained byreacting a compound of Formula I with a suitable acid, e.g.,p-toluenesulfonic acid, trichloroacetic acid or the like.

The preparation of the compounds of this invention is illustrated by thefollowing Examples, wherein temperatures are given in degree Centigrade.

EXAMPLE 1 4-(2-Amino-4-methylpyrimidin-4-yl)-3-butyne-2-ol

A mixture of 10.0 g of 2-amino-4-chloro-6-methylpyrimidine, 8.8 ml of2-methyl-3-butyn-2-ol, 400 ml of tetrahydrofuran (THF), 0.06 g of copper(I) iodide, 0.5 g of bis(triphenylphosphine)palladium (II) chloride and20.4 ml of triethylamine was heated overnight at reflux under a nitrogenatmosphere. The reaction mixture was allowed to cool. It was thenpartitioned between 200 ml of ethyl acetate and 100 ml of sodiumbicarbonate. The organic layer was washed successively with 100 ml ofwater and 100 ml of brine. The organic layer was dried (MgSO₄), filteredand concentrated under reduced pressure. The residue was placed on asilica gel dry column and eluted with dichloromethane/ethyl acetate/THF(10:90:0.1). The product band was extracted with THF. The organicextract was concentrated. Trituration of the residue (butyl chloride)gave 4.44 g of the title compound as a solid, m.p. 155°; PMR (90 MHz,CDCl₃) δ1.65(s, 6H, CH₃), 2.3(s, CH₃, 3H), 2.8(s, OH, 1H), 5.2(bs, 2H,NH₂), 6.6(s, Het-H, 1H); IR(nujol) 2221(w, C.tbd.C) cm⁻¹.

EXAMPLE 2 2-Amino-4-ethynyl-6-methylpyrimidine

A mixture of 4.44 g of 4-(2-amino-4-methylpyrimidin-4-yl)-3-butyne-2-ol,1 g of sodium hydroxide, 5 ml of dioxane and 50 ml of toluene wasrefluxed for two hours. The toluene layer was decanted from the residue,concentrated under reduced pressure and chromatographed on a silica geldry column. The product band eluted with (2:3:0.05) ethylacetate/dichloromethane/THF. Extraction with THF and concentration ofthe solvent gave 0.75 g of the title compound as a solid, 129°-130°dec.; IR(nujol) 2119(w, C.tbd.C) cm⁻¹ ; PMR(60 MHz, CDCl₃) δ2,3(s, CH₃,3H), 3.1(s, C.tbd.CH, 1H), 5.3-5.6(bs, NH₂, 2H), 6.6(s, Het-H, 1H).

EXAMPLE 32-[[(4-Ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoicacid, methyl ester

In a dry flask under a nitrogen atmosphere was mixed 0.24 g of2-amino-4-ethenyl-6-methylpyrimidine, 0.61 g of2-carbomethoxybenzenesulfonylisocyanate and 25 ml of drydichloromethane. The solution was heated to reflux for five minutes andallowed to stir at room temperature overnight. A precipitate formed. Thereaction mixture was stripped, titurated with butyl chloride to give0.56 g of the title compound as a solid, m.p. 185°-190° (dec); IR(nujol)2111 (C.tbd.C), 3250 (NH), 3321 (NH), 1716 (CO) and 1725 (CO) cm⁻¹.

The invention is further exemplified by the compounds of Tables I to XXwhich can be prepared as described in Equations 1-10 and Examples 1-3 orby modifications thereof known to those skilled in the art.

KEY OF GENERAL STRUCTURES

The following structures are designated as shown in Tables I-XX.

    ______________________________________                                        General Structure I                                                           wherein W.sub.1 is O unless otherwise indicated.                               ##STR20##                                                                    General Structure II                                                           ##STR21##                                                                    General Structure III                                                          ##STR22##                                                                    General Structure IV, IVA and IVB                                              ##STR23##                                                                    General Structure V                                                            ##STR24##                                                                    General Structure VI                                                           ##STR25##                                                                    General Structure VII                                                          ##STR26##                                                                    General Structure VIII                                                         ##STR27##                                                                    General Structure IX                                                           ##STR28##                                                                    General Structure X                                                            ##STR29##                                                                    General Structure XI                                                           ##STR30##                                                                    General Structure XII                                                          ##STR31##                                                                    General Structure XIIIA                                                        ##STR32##                                                                    General Structure XIIB                                                         ##STR33##                                                                    General Structure XIII                                                         ##STR34##                                                                    General Structure XIV                                                          ##STR35##                                                                    General Structure XV                                                           ##STR36##                                                                    General Structure XVI                                                          ##STR37##                                                                    General Structure XVII                                                         ##STR38##                                                                    General Structure XVIII                                                        ##STR39##                                                                    General Structure XIX                                                          ##STR40##                                                                    General Structure XX                                                           ##STR41##                                                                    ______________________________________                                    

                                      TABLE I                                     __________________________________________________________________________    General Structure I                                                           R.sub.1    R.sub.2                                                                            R  X        Y      Z  m.p. °C.                         __________________________________________________________________________    OCH.sub.2 CH.sub.2 OCH.sub.3                                                             H    H  CH.sub.3 H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  CH.sub.3 H      CH 185-190°                         CO.sub.2 CH.sub.3                                                                        H    H  OCH.sub.3                                                                              H      CH 173-180°                         CO.sub.2 CH.sub.3                                                                        H    H  OCH.sub.3                                                                              H      N  158-161° (d)                     CO.sub.2 CH.sub.3                                                                        H    CH.sub.3                                                                         OCH.sub.3                                                                              CH.sub.3                                                                             N                                          CO.sub.2 CH.sub.3                                                                        H    H  OCH.sub.3                                                                              C.sub.2 H.sub.5                                                                      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  OCH.sub.3                                                                              (CH.sub.2).sub.2 CH.sub.3                                                            N                                          CO.sub.2 C.sub.2 H.sub.5                                                                 H    H  CH.sub.3 H      N                                          CO.sub.2 C.sub.2 H.sub.5                                                                 H    H  OCH.sub.3                                                                              H      CH                                         CO.sub.2 C.sub.2 H.sub.5                                                                 H    H  OCH.sub.3                                                                              H      N                                          CO.sub.2 CH(CH.sub.3).sub.2                                                              H    H  CH.sub.3 H      CH                                         CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                       H    H  OCH.sub.3                                                                              H      N                                          CO.sub.2 CH.sub.2 CH═CH.sub.2                                                        H    H  OCH.sub. 3                                                                             H      CH                                         CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                            H    H  OCH.sub.3                                                                              H      CH                                         CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     H    H  OCH.sub.3                                                                              H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  C.sub.2 H.sub.5                                                                        H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  OC.sub.2 H.sub.5                                                                       H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  OC.sub.2 H.sub.5                                                                       H      N  150-153°                         CO.sub.2 CH.sub.3                                                                        H    H  CH.sub.2 OCH.sub.3                                                                     H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  CH.sub.2 OC.sub.2 H.sub.5                                                              H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  OCH.sub.2 CF.sub.3                                                                     H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  OCH.sub.2 CF.sub.2 H                                                                   H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  OCH.sub.2 CH.sub.2 F                                                                   H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  OCF.sub.2 H                                                                            H      CH                                         CO.sub.2 CH.sub.3                                                                        5-Cl H  CH.sub.3 H      CH                                         CO.sub.2 CH.sub.3                                                                        5-OCH.sub.3                                                                        H  OCH.sub.3                                                                              H      N                                          CO.sub.2 CH.sub.3                                                                        5-CH.sub.3                                                                         H  OCH.sub.3                                                                              H      CH                                         CO.sub.2 CH.sub.3                                                                        3-F  H  CH.sub.3 H      CH                                         CO.sub.2 CH.sub.3                                                                        5-Br H  OCH.sub.3                                                                              H      N                                          CO.sub.2 CH.sub.3                                                                        5-OCF.sub.2 H                                                                      H  OCH.sub.3                                                                              H      CH                                         SO.sub.2 N(CH.sub.3).sub.2                                                               H    H  CH.sub.3 H      CH                                         SO.sub.2 N(CH.sub.3).sub.2                                                               H    H  OCH.sub.3                                                                              H      CH                                         SO.sub.2 N(CH.sub.3).sub.2                                                               H    H  OCH.sub.3                                                                              H      N  135-139° (d)                     SO.sub.2 N(CH.sub.3).sub.2                                                               H    H  OC.sub.2 H.sub.5                                                                       H      N  150-153°                         SO.sub.2 N(CH.sub.3)C.sub.2 H.sub.5                                                      H    H  OCH.sub.3                                                                              H      CH                                         SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                        H    H  CH.sub.3 H      CH                                         SO.sub.2 NCH.sub.2 H.sub.5                                                               H    H  OCH.sub.3                                                                              H      CH                                         SO.sub.2 N(CH.sub.3)CH(CH.sub.3).sub.2                                                   H    H  OCH.sub.3                                                                              H      N                                          SO.sub.2 N(OCH.sub.3)CH.sub.3                                                            H    H  CH.sub.3 H      CH                                         OSO.sub.2 CH.sub.3                                                                       H    H  OCH.sub.3                                                                              H      CH                                         OSO.sub.2 CH.sub.3                                                                       H    H  OCH.sub.3                                                                              H      N                                          OSO.sub.2 C.sub.2 H.sub.5                                                                H    H  CH.sub.3 H      CH                                         OSO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                      H    H  OCH.sub.3                                                                              H      N                                          OSO.sub.2 N(CH.sub.3).sub.2                                                              H    H  OCH.sub.3                                                                              H      CH                                         OCF.sub.3  H    H  CH.sub.3 H      CH                                         SCF.sub.3  H    H  OCH.sub.3                                                                              H      N                                          OCF.sub.2 H                                                                              H    H  OCH.sub.3                                                                              H      N                                          SCF.sub.2 H                                                                              H    H  OCH.sub.3                                                                              H      CH                                         SO.sub.2 CF.sub.2 H                                                                      H    H  CH.sub.3 H      CH                                         OCH.sub.2 CH═CH.sub.2                                                                H    H  OCH.sub.3                                                                              H      N                                          OCH.sub.2 CH═CH.sub.2                                                                H    H  OCH.sub.3                                                                              H      CH                                         OCH.sub.2 C(CH.sub.3)═CH.sub.2                                                       H    H  CH.sub.3 H      CH                                         OCH.sub.2 C(CH.sub.3)═CH.sub.2                                                       H    H  OCH.sub.3                                                                              H      N                                          OCH.sub.2 C.tbd.CH                                                                       H    H  OCH.sub.3                                                                              H      N                                          OCH.sub.2 C.tbd.CH                                                                       H    H  CH.sub.3 H      CH                                         OCH.sub.2 C.tbd.CCH.sub.3                                                                H    H  OCH.sub.3                                                                              H      N                                          OCH.sub.2 C.tbd.CCH.sub.3                                                                H    H  CH.sub.3 H      CH                                         CH.sub.2 OCH.sub.3                                                                       H    H  OCH.sub.3                                                                              H      N                                          CH.sub.2 OCH.sub.3                                                                       H    H  CH.sub.3 H      CH                                         (CH.sub.2).sub.2 OC.sub.2 H.sub.5                                                        H    H  CH.sub.3 H      CH                                         (CH.sub.2).sub.2 OC.sub.2 H.sub.5                                                        H    H  OCH.sub.3                                                                              H      N                                          C.sub.6 H.sub.5                                                                          H    H  OCH.sub.3                                                                              H      N                                          C.sub.6 H.sub.5                                                                          H    H  OCH.sub.3                                                                              H      CH                                         C.tbd.CCH.sub.3                                                                          H    H  OCH      H      N                                           C.tbd.CCH.sub.3                                                                         H    H  OCH.sub.3                                                                              H      CH                                         CH.sub.2 C.tbd.CCH.sub.3                                                                 H    H  CH.sub.3 H      CH                                         CH.sub.2 C.tbd.CCH.sub.3                                                                 H    H  OCH.sub.3                                                                              H      N                                          CH═CHCF.sub.3                                                                        H    H  OCH.sub.3                                                                              H      CH                                         CH═CHCF.sub.3                                                                        H    H  OCH.sub.3                                                                              H      N                                          CH═CHBr                                                                              H    H  CH.sub.3 H      CH                                         CH═CHBr                                                                              H    H  OCH.sub.3                                                                              H      N                                          Q-1        H    H  OCH.sub.3                                                                              H      N                                          Q-1        H    H  OCH.sub.3                                                                              H      CH                                         Q-2        H    H  OCH.sub.3                                                                              H      N                                          Q-2        H    H  OCH.sub.3                                                                              H      CH                                         Q-3        H    H  OCH.sub.3                                                                              H      N                                          Q-3        H    H  OCH.sub.3                                                                              H      CH                                         Q-4        H    H  OCH.sub.3                                                                              H      N                                          Q-4        H    H  OCH.sub.3                                                                              H      CH                                         Q-5        H    H  OCH.sub.3                                                                              H      N                                          Q-5        H    H  OCH.sub.3                                                                              H      CH                                         Q-6        H    H  OCH.sub.3                                                                              H      N                                          Q-6        H    H  OCH.sub.3                                                                              H      CH                                         Q-7        H    H  OCH.sub.3                                                                              H      N                                          Q-7        H    H  OCH.sub.3                                                                              H      CH                                         Q-8        H    H  OCH.sub.3                                                                              H      N                                          Q-8        H    H  OCH.sub.3                                                                              H      CH                                         Q-9        H    H  OCH.sub.3                                                                              H      N                                          Q-9        H    H  OCH.sub.3                                                                              H      CH                                         Q-10       H    H  OCH.sub.3                                                                              H      N                                          Q-10       H    H  OCH.sub.3                                                                              H      CH                                         Q-11       H    H  OCH.sub.3                                                                              H      N                                          Q-11       H    H  OCH.sub.3                                                                              H      CH                                         Q-12       H    H  OCH.sub.3                                                                              H      N                                          Q-12       H    H  OCH.sub.3                                                                              H      CH                                         Q-13       H    H  OCH.sub.3                                                                              H      N                                          Q-13       H    H  OCH.sub.3                                                                              H      CH                                         Q-14       H    H  OCH.sub.3                                                                              H      N                                          Q-14       H    H  CH.sub.3 H      CH                                         Q-15       H    H  CH.sub.3 H      CH                                         Q-15       H    H  OCH.sub.3                                                                              H      N                                          Q-16       H    H  OCH.sub.3                                                                              H      N                                          Q-16       H    H  CH.sub.3 H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  OCH.sub.3                                                                              (CH.sub.2).sub.3 CH.sub.3                                                            CH 134-136                                 CO.sub.2 CH.sub.3                                                                        H    H  CH.sub.3 (CH.sub.2).sub.3 CH.sub.3                                                            CH 129-131                                 CO.sub.2 CH.sub.3                                                                        H    H  OCH.sub.3                                                                              (CH.sub.2).sub.3 CH.sub.3                                                            N                                          *CO.sub.2 CH.sub.3                                                                       H    H  OCH.sub.3                                                                              H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  CH.sub.2 CH.sub.2 CH.sub.3                                                             H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  OCH.sub.2 CH.sub.2 CH.sub.3                                                            H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  CH.sub.2 Br                                                                            H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  OCH.sub.2 CH.sub.2 CH.sub.2 F                                                          H      CH                                         CO.sub. 2 CH.sub.3                                                                       H    H  NHCH.sub.3                                                                             H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  1-cyclopropyl                                                                          H      CH                                         CO.sub.2 CH.sub.3                                                                        H    H  CH.sub.3 Br     N                                          CO.sub.2 CH.sub.3                                                                        H    H  CH.sub.3 I      N                                          CO.sub.2 CH.sub.3                                                                        H    H  OCH.sub.3                                                                              2-Cl-C.sub.6 H.sub.4                                                                 CH                                         CO.sub.2 CH.sub.3                                                                        H    H  OCH.sub.3                                                                              2-SCH.sub.3 -C.sub.6 H.sub.4                                                         CH                                         CO.sub.2 CH.sub.3                                                                        H    H  CH.sub.3 C(CH.sub.3).sub.2 OH                                                                 CH 151-153° (d)                     CO.sub.2 CH.sub.3                                                                        H    H  OCH.sub.3                                                                              C(CH.sub.3).sub.2 OH                                                                 CH 156°                             CO.sub.2 CH.sub.3                                                                        H    H  N(CH.sub.3).sub.2                                                                      (CH.sub.2).sub.3 CH.sub.3                                                            CH 168-169° (d)                     SO.sub.2 N(CH.sub.3).sub.2                                                               H    H  N(CH.sub.3).sub.2                                                                      (CH.sub.2).sub.3 CH.sub.3                                                            CH 166°                             CO.sub.2 CH.sub.3                                                                        H    H  CH.sub.3 C.sub.6 H.sub.5                                                                      CH 187-189°                         CO.sub.2 CH.sub.2 CH.sub.3                                                               H    H  CH.sub.3 C.sub.6 H.sub.5                                                                      CH 184-188°                         SO.sub.2 N(CH.sub.3).sub.2                                                               H    H  CH.sub.3 C.sub.6 H.sub.5                                                                      CH 179-185°                         CO.sub.2 CH.sub.3                                                                        H    H  OCH.sub. 3                                                                             C.sub.6 H.sub.5                                                                      CH 195-197°                         __________________________________________________________________________     *W.sub.1 is sulfur                                                       

                  TABLE 1A                                                        ______________________________________                                        General Structure I                                                           R.sub.1                                                                            R.sub.2                                                                             R     X      Y       Z    R.sub.25                                                                            m.p. °C.                    ______________________________________                                        Q-17 H     H     OCH.sub.3                                                                            H       CH   H                                        Q-17 H     H     CH.sub.3                                                                             H       N    CH.sub.3                                 Q-18 H     H     OCH.sub.3                                                                            H       CH   H                                        Q-18 H     H     CH.sub.3                                                                             H       CH   CH.sub.3                                 Q-19 H     H     OCH.sub.3                                                                            H       N    H                                        Q-19 H     H     OCH.sub.3                                                                            CH.sub.3                                                                              CH   CH.sub.3                                 Q-20 H     H     CH.sub.3                                                                             (CH.sub.2).sub.3 CH.sub.3                                                             CH   H                                        Q-20 H     H     OCH.sub.3                                                                            H       N    CH.sub.3                                 ______________________________________                                    

                  TABLE II                                                        ______________________________________                                        General Structure II                                                          R3          R      X         Y        Z                                       ______________________________________                                        H           H      CH.sub.3  H        CH                                      H           H      OCH.sub.3 H        N                                       CH.sub.3    H      CH.sub.3  H        CH                                      CH.sub.3    H      OCH.sub.3 H        CH                                      CH.sub.3    H      OCH.sub.3 H        N                                       OCH.sub.3   H      CH.sub.3  H        CH                                      OCH.sub.3   H      OCH.sub.3 H        CH                                      OCH.sub.3   H      OCH.sub.3 H        N                                       F           H      OCH.sub.3 H        CH                                      Cl          H      CH.sub.3  H        CH                                      Cl          H      OCH.sub.3 H        CH                                      Cl          H      OCH.sub.3 H        N                                       Cl          H      CH.sub.3  H        N                                       Cl          H      OCH.sub.3 CH.sub.3 CH                                      Cl          H      CH.sub.3  C.sub.2 H.sub.5                                                                        CH                                      Cl          H      OCH.sub.3 (CH.sub.2).sub.2 CH.sub.3                                                              CH                                      Cl          CH.sub.3                                                                             OCH.sub.3 H        CH                                      Br          H      CH.sub.3  H        CH                                      Br          H      OCH.sub.3 H        CH                                      Br          H      OCH.sub.3 H        N                                       SO.sub.2 N(CH.sub.3).sub.2                                                                H      CH.sub.3  H        CH                                      SO.sub.2 N(CH.sub.3).sub.2                                                                H      OCH.sub.3 H        CH                                      SO.sub.2 N(CH.sub.3).sub.2                                                                H      OCH.sub.3 H        N                                       OSO.sub.2 CH.sub.3                                                                        H      OCH.sub.3 H        CH                                      OSO.sub.2 CH.sub.3                                                                        H      OCH.sub.3 H        N                                       OSO.sub.2 CH.sub.3                                                                        H      CH.sub.3  H        CH                                      SCH.sub.3   H      OCH.sub.3 H        N                                       SCH.sub.3   H      CH.sub.3  H        CH                                      SCH.sub.3   H      OCH.sub.3 H        CH                                      SO.sub.2 CH.sub.3                                                                         H      OCH.sub.3 H        N                                       SO.sub.2 CH.sub.3                                                                         H      OCH.sub.3 H        CH                                      SO.sub.2 CH.sub.3                                                                         H      CH.sub.3  H        CH                                      SO.sub.2 CH.sub.3                                                                         H      OCH.sub.3 (CH.sub.2).sub.3 CH.sub.3                                                              CH                                      SO.sub.2 CH.sub.3                                                                         H      CH.sub.3  (CH.sub.2).sub.3 CH.sub.3                                                              CH                                      ______________________________________                                    

                  TABLE III                                                       ______________________________________                                        General Structure III                                                         R.sub.4        R      X       Y        Z                                      ______________________________________                                        CH.sub.3       H      CH.sub.3                                                                              H        CH                                     CH.sub.3       H      OCH.sub.3                                                                             H        CH                                     CH.sub.3       H      OCH.sub.3                                                                             H        N                                      CH.sub.3       H      CH.sub.3                                                                              H        N                                      C.sub.2 H.sub.5                                                                              H      OCH.sub.3                                                                             H        CH                                     C.sub.2 H.sub.5                                                                              H      OCH.sub.3                                                                             H        N                                      C.sub.2 H.sub.5                                                                              H      CH.sub.3                                                                              H        CH                                     OCH.sub.3      H      CH.sub.3                                                                              H        CH                                     OCH.sub.3      H      OCH.sub.3                                                                             H        CH                                     OCH.sub.3      H      OCH.sub.3                                                                             H        N                                      OCH.sub.3      H      CH.sub.3                                                                              H        N                                      OC.sub.2 H.sub.5                                                                             H      OCH.sub.2                                                                             H        CH                                     OC.sub.2 H.sub.5                                                                             H      OCH.sub.3                                                                             H        N                                      F              H      CH.sub.3                                                                              H        CH                                     F              H      OCH.sub.3                                                                             H        CH                                     Cl             H      CH.sub.3                                                                              H        CH                                     Cl             H      OCH.sub.3                                                                             H        N                                      Cl             H      OCH.sub.3                                                                             H        CH                                     Cl             H      CH.sub.3                                                                              H        N                                      Cl             H      OCH.sub.3                                                                             CH.sub.3 N                                      Cl             H      OCH.sub.3                                                                             C.sub.2 H.sub.5                                                                        CH                                     Cl             H      OCH.sub.3                                                                             (CH.sub.2).sub.2 CH.sub.3                                                              CH                                     Cl             CH.sub.3                                                                             OCH.sub.3                                                                             H        N                                      Br             H      CH.sub.3                                                                              H        CH                                     Br             H      OCH.sub.3                                                                             H        CH                                     Br             H      OCH.sub.3                                                                             H        N                                      SO.sub.2 N(CH.sub.3).sub.2                                                                   H      CH.sub.3                                                                              H        CH                                     SO.sub.2 N(CH.sub.3).sub.2                                                                   H      OCH.sub.3                                                                             H        CH                                     SO.sub.2 N(CH.sub.3).sub.2                                                                   H      OCH.sub.3                                                                             H        N                                      SO.sub.2 N(CH.sub.3).sub.2                                                                   H      CH.sub.3                                                                              H        N                                      SO.sub.2 NHCH.sub.3                                                                          H      OCH.sub.3                                                                             H        CH                                     SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                            H      OCH.sub.3                                                                             H        N                                      SO.sub.2 N(CH.sub.3)(CH.sub.2).sub.2 CH.sub.3                                                H      CH.sub.3                                                                              H        CH                                     SO.sub.2 N(OCH.sub.3)CH.sub.3                                                                H      CH.sub.3                                                                              H        CH                                     SO.sub.2 N(OCH.sub.3)CH.sub.3                                                                H      OCH.sub.3                                                                             H        CH                                     SO.sub.2 N(OCH.sub.3)CH.sub.3                                                                H      OCH.sub.3                                                                             H        N                                      SCH.sub.3      H      OCH.sub.3                                                                             H        N                                      SO.sub.2 CH.sub.3                                                                            H      CH.sub.3                                                                              H        CH                                     SO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                             H        N                                      SO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                             H        CH                                     SC.sub.2 H.sub.5                                                                             H      CH.sub.3                                                                              H        CH                                     SO.sub.2 C.sub.2 H.sub.5                                                                     H      OCH.sub.3                                                                             H        N                                      SO.sub.2 C.sub.2 H.sub.5                                                                     N      OCH.sub.3                                                                             H        N                                      S(CH.sub.2).sub.2 CH.sub.3                                                                   H      OCH.sub. 3                                                                            H        CH                                     SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                           H      OCH.sub.3                                                                             H        N                                      SCH.sub.2 CH═CH.sub.2                                                                    H      CH.sub.3                                                                              H        CH                                     SO.sub.2 CH.sub.2 CH═CH.sub.2                                                            H      OCH.sub.3                                                                             H        CH                                     SO.sub.2 CH.sub.2 CH═CH.sub.2                                                            H      OCH.sub.3                                                                             H        N                                      OCH.sub.2 CH═CH.sub.2                                                                    H      CH.sub.3                                                                              H        CH                                     OCH.sub.2 CH═CH.sub.2                                                                    H      OCH.sub.3                                                                             H        CH                                     OCH.sub.2 CH═CH.sub.2                                                                    H      OCH.sub.3                                                                             H        N                                      OCH(CH.sub.3)═CH.sub.2                                                                   H      CH.sub.3                                                                              H        CH                                     OCH(CH.sub.3)═CH.sub.2                                                                   H      OCH.sub.3                                                                             H        N                                      OCH(CH.sub.3)═CH.sub.2                                                                   H      OCH.sub.3                                                                             H        N                                      CH.sub.2 OCH.sub.3                                                                           H      CH.sub.3                                                                              H        N                                      CH.sub.2 OCH.sub.3                                                                           H      OCH.sub.3                                                                             H        N                                      CH.sub.2 OCH.sub.3                                                                           H      OCH.sub.3                                                                             H        CH                                     CH.sub.2 OCH.sub.3                                                                           H      CH.sub.3                                                                              H        CH                                     CH.sub.2 OC.sub.2 H.sub.5                                                                    H      CH.sub.3                                                                              H        CH                                     CH.sub.2 OC.sub.2 H.sub.5                                                                    H      OCH.sub.3                                                                             H        CH                                     CH.sub.2 OC.sub.2 H.sub.5                                                                    H      OCH.sub.3                                                                             H        N                                      SO.sub.2 N(CH.sub.3).sub.2                                                                   H      OCH.sub.3                                                                             (CH.sub.2).sub.3 CH.sub.3                                                              CH                                     ______________________________________                                    

                  TABLE IV                                                        ______________________________________                                        General Structure IV                                                          L     R.sub.5       R       X     Y       Z                                   ______________________________________                                        L-4   CO.sub.2 CH.sub.3                                                                           H       CH.sub.3                                                                            H       CH                                  L-4   CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                           H       N                                   L-4   CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                           H       CH                                  L-4   CO.sub.2 CH.sub.3                                                                           H       CH.sub.3                                                                            H       N                                   L-4   CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                           CH.sub.3                                                                              N                                   L-4   CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                           C.sub.2 H.sub.5                                                                       CH                                  L-4   CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                           (CH.sub.2).sub.2 CH.sub.3                                                             CH                                  L-4   CO.sub.2 C.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                           H       CH                                  L-4   CO.sub.2 C.sub.2 H.sub.5                                                                    H       CH.sub.3                                                                            H       CH                                  L-4   CO.sub.2 C.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                           H       N                                   L-4   CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H       OCH.sub.3                                                                           H       CH                                  L-4   CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H       OCH.sub.3                                                                           H       N                                   L-4   CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3                                                         H       CH.sub.3                                                                            H       CH                                  L-4   CO.sub.2 CH.sub.2 CH = CH.sub.2                                                             H       OCH.sub.3                                                                           H       N                                   L-4   CO.sub.2 (CH.sub.2).sub.2 Cl                                                                H       OCH.sub.3                                                                           H       CH                                  L-4   CH.sub.3      H       CH.sub.3                                                                            H       CH                                  L-4   CH.sub.3      H       OCH.sub.3                                                                           H       N                                   L-4   CH.sub.3      H       OCH.sub.3                                                                           H       CH                                  L-4   C.sub.2 H.sub.5                                                                             H       CH.sub.3                                                                            H       CH                                  L-4   (CH.sub.2).sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                           H       CH                                  L-4   Cl            H       CH.sub.3                                                                            H       CH                                  L-4   Cl            H       OCH.sub.3                                                                           H       N                                   L-4   Cl            H       OCH.sub.3                                                                           H       CH                                  L-4   F             H       OCH.sub.3                                                                           H       CH                                  L-4   Br            H       CH.sub.3                                                                            H       CH                                  L-4   Br            H       OCH.sub.3                                                                           H       N                                   L-4   Br            H       OCH.sub.3                                                                           H       CH                                  L-4   NO.sub.2      H       CH.sub.3                                                                            H       N                                   L-4   NO.sub.2      H       OCH.sub.3                                                                           H       N                                   L-4   NO.sub.2      H       OCH.sub.3                                                                           H       CH                                  L-4   NO.sub.2      H       CH.sub.3                                                                            H       CH                                  L-4   SO.sub.2 N(CH.sub.3).sub.2                                                                  H       CH.sub.3                                                                            H       N                                   L-4   SO.sub.2 N(CH.sub.3).sub.2                                                                  H       OCH.sub.3                                                                           H       N                                   L-4   SO.sub.2 N(CH.sub.3).sub.2                                                                  H       OCH.sub.3                                                                           H       CH                                  L-4   SO.sub.2 N(CH.sub.3).sub.2                                                                  H       CH.sub.3                                                                            H       CH                                  L-4   SO.sub.2 N(CH.sub.3)C.sub.2 H.sub.5                                                         H       OCH.sub.3                                                                           H       N                                   L-4   SO.sub.2 NHC.sub.2 H.sub.5                                                                  H       OCH.sub.3                                                                           H       CH                                  L-4   SO.sub.2 NHCH(CH.sub.3).sub.2                                                               H       OCH.sub.3                                                                           H       CH                                  L-4   SO.sub.2 N(OCH.sub.3)CH.sub.3                                                               H       OCH.sub.3                                                                           H       N                                   L-4   SO.sub.2 N(OCH.sub.3)CH.sub.3                                                               H       CH.sub.3                                                                            H       CH                                  L-4   SO.sub.2 N(OCH.sub.3)CH.sub.3                                                               H       OCH.sub.3                                                                           H       CH                                  L-4   SCH.sub.3     H       CH.sub.3                                                                            H       CH                                  L-4   SCH.sub.3     H       OCH.sub.3                                                                           H       CH                                  L-4   SCH.sub.3     H       OCH.sub.3                                                                           H       N                                   L-4   SO.sub.2 CH.sub.3                                                                           H       CH.sub.3                                                                            H       N                                   L-4   SO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                           H       N                                   L-4   SO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                           H       CH                                  L-4   SO.sub.2 CH.sub.3                                                                           H       CH.sub.3                                                                            H       CH                                  L-4   SC.sub.2 H.sub.5                                                                            H       OCH.sub.3                                                                           H       N                                   L-4   SC.sub.2 H.sub.5                                                                            H       OCH.sub.3                                                                           H       CH                                  L-4   SC.sub.2 H.sub.5                                                                            H       CH.sub.3                                                                            H       CH                                  L-4   SO.sub.2 C.sub.2 H.sub.5                                                                    H       CH.sub.3                                                                            H       CH                                  L-4   SO.sub.2 C.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                           H       N                                   L-4   SO.sub.2 C.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                           H       CH                                  L-4   S(CH.sub.2).sub.2 CH.sub.3                                                                  H       OCH.sub.3                                                                           H       N                                   L-4   SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H       OCH.sub.3                                                                           H       CH                                  L-4   SCH.sub.2 CH═CH                                                                         H       OCH.sub.3                                                                           H       N                                   L-4   SO.sub.2 CH.sub.2 CH═CH.sub.2                                                           H       OCH.sub.3                                                                           H       CH                                  L-4   CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              OCH.sub.3                                                                           H       CH                                  L-4   SO.sub.2 N(CH.sub.3).sub.2                                                                  CH.sub.3                                                                              OCH.sub.3                                                                           H       CH                                  L-4   SO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              OCH.sub.3                                                                           H       CH                                  L-4   NO.sub.2      CH.sub.3                                                                              OCH.sub.3                                                                           H       CH                                  L-4   Cl            CH.sub.3                                                                              OCH.sub.3                                                                           H       CH                                  L-4   CH.sub.3      CH.sub.3                                                                              OCH.sub.3                                                                           H       CH                                  L-4   CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                           (CH.sub.2).sub.3 CH.sub.3                                                             CH                                  L-4   CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                           (CH.sub.2).sub.3 CH.sub.3                                                             N                                   L-4   SO.sub.2 N(CH.sub.3).sub.2                                                                  H       OCH.sub.3                                                                           (CH.sub.2).sub.3 CH.sub.3                                                             CH                                  ______________________________________                                    

                  TABLE IVA                                                       ______________________________________                                        General Structure IVA                                                         L    R.sub.5       R      X     Y    Z    m.p. °C.                     ______________________________________                                        L-5  CO.sub.2 CH.sub.3                                                                           H      CH.sub.3                                                                            H    CH                                       L-5  CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           H    N    176-179                             L-5  CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           H    CH                                       L-5  CO.sub.2 CH.sub.3                                                                           H      CH.sub.3                                                                            H    N                                        L-5  CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           CH.sub.3                                                                           N                                        L-5  CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH                                       L-5  CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           H    CH                                       L-5  CO.sub.2 C.sub.2 H.sub.5                                                                    H      CH.sub.3                                                                            H    CH                                       L-5  CO.sub.2 C.sub.2 H.sub.5                                                                    H      OCH.sub.3                                                                           H    N                                        L-5  CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H      OCH.sub.3                                                                           H    CH                                       L-5  CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H      OCH.sub.3                                                                           H    N                                        L-5  CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3                                                         H      CH.sub.3                                                                            H    CH                                       L-5  CO.sub.2 CH.sub.2 CH═CH.sub.2                                                           H      OCH.sub.3                                                                           H    N                                        L-5  CO.sub.2 (CH.sub.2).sub.2 Cl                                                                H      OCH.sub.3                                                                           H    CH                                       L-5  CH.sub.3      H      CH.sub.3                                                                            H    CH                                       L-5  CH.sub.3      H      OCH.sub.3                                                                           H    N                                        L-5  CH.sub.3      H      OCH.sub.3                                                                           H    CH                                       L-5  C.sub.2 H.sub.5                                                                             H      CH.sub.3                                                                            H    CH                                       L-5  (CH.sub.2).sub.2 CH.sub.3                                                                   H      OCH.sub.3                                                                           H    CH                                       L-5  Cl            H      CH.sub.3                                                                            H    CH                                       L-5  Cl            H      OCH.sub.3                                                                           H    N                                        L-5  Cl            H      OCH.sub.3                                                                           H    CH                                       L-5  F             H      OCH.sub.3                                                                           H    CH                                       L-5  Br            H      CH.sub.3                                                                            H    CH                                       L-5  Br            H      OCH.sub.3                                                                           H    N                                        L-5  Br            H      OCH.sub.3                                                                           H    CH                                       L-5  NO.sub.2      H      CH.sub.3                                                                            H    N                                        L-5  NO.sub.2      H      OCH.sub.3                                                                           H    N                                        L-5  NO.sub.2      H      OCH.sub.3                                                                           H    CH                                       L-5  NO.sub.2      H      CH.sub.3                                                                            H    CH                                       L-5  SO.sub.2 N(CH.sub.3).sub.2                                                                  H      CH.sub.3                                                                            H    N                                        L-5  SO.sub.2 N(CH.sub.3).sub.2                                                                  H      OCH.sub.3                                                                           H    N                                        L-5  SO.sub.2 N(CH.sub.3).sub.2                                                                  H      OCH.sub.3                                                                           H    CH                                       L-5  SO.sub.2 N(CH.sub.3 ).sub.2                                                                 H      CH.sub.3                                                                            H    CH                                       L-5  SO.sub.2 N(CH.sub.3)C.sub.2 H.sub.5                                                         H      OCH.sub.3                                                                           H    N                                        L-5  SO.sub.2 NHC.sub.2 H.sub.5                                                                  H      OCH.sub.3                                                                           H    CH                                       L-5  SO.sub.2 NHCH(CH.sub.3).sub.2                                                               H      OCH.sub.3                                                                           H    CH                                       L-5  SO.sub.2 N(OCH.sub.3)CH.sub.3                                                               H      OCH.sub.3                                                                           H    N                                        L-5  SO.sub.2 N(OCH.sub.3)CH.sub.3                                                               H      CH.sub.3                                                                            H    CH                                       L-5  SO.sub.2 N(OCH.sub.3)CH.sub.3                                                               H      OCH.sub.3                                                                           H    CH                                       L-5  SCH.sub.3     H      CH.sub.3                                                                            H    CH                                       L-5  SCH.sub.3     H      OCH.sub.3                                                                           H    CH                                       L-5  SCH.sub.3     H      OCH.sub.3                                                                           H    N                                        L-5  SO.sub.2 CH.sub.3                                                                           H      CH.sub.3                                                                            H    N                                        L-5  SO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           H    N                                        L-5  SO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           H    CH                                       L-5  SO.sub.2 CH.sub.3                                                                           H      CH.sub.3                                                                            H    CH                                       L-5  SC.sub.2 H.sub.5                                                                            H      OCH.sub.3                                                                           H    N                                        L-5  SC.sub.2 H.sub.5                                                                            H      OCH.sub.3                                                                           H    CH                                       L-5  SC.sub.2 H.sub.5                                                                            H      CH.sub.3                                                                            H    CH                                       L-5  SO.sub.2 C.sub.2 H.sub.5                                                                    H      CH.sub.3                                                                            H    CH                                       L-5  SO.sub.2 C.sub.2 H.sub.5                                                                    H      OCH.sub.3                                                                           H    N                                        L-5  SO.sub.2 C.sub.2 H.sub.5                                                                    H      OCH.sub.3                                                                           H    CH                                       L-5  S(CH.sub.2).sub.2 CH.sub.3                                                                  H      OCH.sub.3                                                                           H    N                                        L-5  SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H      OCH.sub.3                                                                           H    CH                                       L-5  SCH.sub.2 CH═CH.sub.2                                                                   H      OCH.sub.3                                                                           H    N                                        L-5  SO.sub.2 CH.sub.2 CH═CH.sub.2                                                           H      OCH.sub.3                                                                           H    CH                                       L-5  CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                             OCH.sub.3                                                                           H    CH                                       L-5  SO.sub.2 N(CH.sub.3).sub.2                                                                  CH.sub.3                                                                             OCH.sub.3                                                                           H    CH                                       L-5  SO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                             OCH.sub.3                                                                           H    CH                                       L-5  NO.sub.2      CH.sub.3                                                                             OCH.sub.3                                                                           H    CH                                       L-5  Cl            CH.sub.3                                                                             OCH.sub.3                                                                           H    CH                                       L-5  CH.sub.3      CH.sub.3                                                                             OCH.sub.3                                                                           H    CH                                       L-5  CO.sub.2 CH.sub.3                                                                           H      CH.sub.3                                                                            C.sub.6 H.sub.5                                                                    CH   187-189°                     L-5  CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           C.sub.6 H.sub.5                                                                    CH   123-125°                     L-5  CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           H    CH   182-184°                                                               (d)                                 ______________________________________                                    

                  TABLE IVB                                                       ______________________________________                                        General Structure IVB                                                         L     R.sub.5       R      X     Y       Z                                    ______________________________________                                        L-6   CO.sub.2 CH.sub.3                                                                           H      CH.sub.3                                                                            H       CH                                   L-6   CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           H       N                                    L-6   CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           H       CH                                   L-6   CO.sub.2 CH.sub.3                                                                           H      CH.sub.3                                                                            H       N                                    L-6   CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           CH.sub.3                                                                              N                                    L-6   CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           C.sub.2 H.sub.5                                                                       CH                                   L-6   CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           (CH.sub.2).sub.3 CH.sub.3                                                             CH                                   L-6   CO.sub.2 C.sub.2 H.sub.5                                                                    H      OCH.sub.3                                                                           H       CH                                   L-6   CO.sub.2 C.sub.2 H.sub.5                                                                    H      CH.sub.3                                                                            H       CH                                   L-6   CO.sub.2 C.sub.2 H.sub.5                                                                    H      OCH.sub.3                                                                           H       N                                    L-6   CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H      OCH.sub.3                                                                           H       CH                                   L-6   CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H      OCH.sub.3                                                                           H       N                                    L-6   CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3                                                         H      CH.sub.3                                                                            H       CH                                   L-6   CO.sub.2 CH.sub.2 CH═CH.sub.2                                                           H      OCH.sub.3                                                                           H       N                                    L-6   CO.sub.2 (CH.sub.2).sub.2 Cl                                                                H      OCH.sub.3                                                                           H       CH                                   L-6   CH.sub.3      H      CH.sub.3                                                                            H       CH                                   L-6   CH.sub.3      H      OCH.sub.3                                                                           H       N                                    L-6   CH.sub.3      H      OCH.sub.3                                                                           H       CH                                   L-6   C.sub.2 H.sub.5                                                                             H      CH.sub.3                                                                            H       CH                                   L-6   (CH.sub.2).sub.2 CH.sub.3                                                                   H      OCH.sub.3                                                                           H       CH                                   L-6   Cl            H      CH.sub.3                                                                            H       CH                                   L-6   Cl            H      OCH.sub.3                                                                           H       N                                    L-6   Cl            H      OCH.sub.3                                                                           H       CH                                   L-6   F             H      OCH.sub.3                                                                           H       CH                                   L-6   Br            H      CH.sub.3                                                                            H       CH                                   L-6   Br            H      OCH.sub.3                                                                           H       N                                    L-6   Br            H      OCH.sub.3                                                                           H       CH                                   L-6   NO.sub.2      H      CH.sub.3                                                                            H       N                                    L-6   NO.sub.2      H      OCH.sub.3                                                                           H       N                                    L-6   NO.sub.2      H      OCH.sub.3                                                                           H       CH                                   L-6   NO.sub.2      H      CH.sub.3                                                                            H       CH                                   L-6   SO.sub.2 N(CH.sub.3).sub.2                                                                  H      CH.sub.3                                                                            H       N                                    L-6   SO.sub.2 N(CH.sub.3).sub.2                                                                  H      OCH.sub.3                                                                           H       N                                    L-6   SO.sub. 2 N(CH.sub.3).sub.2                                                                 H      OCH.sub.3                                                                           H       CH                                   L-6   SO.sub.2 N(CH.sub.3).sub.2                                                                  H      CH.sub.3                                                                            H       CH                                   L-6   SO.sub.2 N(CH.sub.3)C.sub.2 H.sub.5                                                         H      OCH.sub.3                                                                           H       N                                    L-6   SO.sub.2 NHC.sub.2 H.sub.5                                                                  H      OCH.sub.3                                                                           H       CH                                   L-6   SO.sub.2 NHCH(CH.sub.3).sub.2                                                               H      OCH.sub.3                                                                           H       CH                                   L-6   SO.sub.2 N(OCH.sub.3)CH.sub.3                                                               H      OCH.sub.3                                                                           H       N                                    L-6   SO.sub.2 N(OCH.sub.3)CH.sub.3                                                               H      CH.sub.3                                                                            H       CH                                   L-6   SO.sub.2 N(OCH.sub.3)CH.sub.3                                                               H      OCH.sub.3                                                                           H       CH                                   L-6   SCH.sub.3     H      CH.sub.3                                                                            H       CH                                   L-6   SCH.sub.3     H      OCH.sub.3                                                                           H       CH                                   L-6   SCH.sub.3     H      OCH.sub.3                                                                           H       N                                    L-6   SO.sub.2 CH.sub.3                                                                           H      CH.sub.3                                                                            H       N                                    L-6   SO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           H       N                                    L-6   SO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           H       CH                                   L-6   SO.sub.2 CH.sub.3                                                                           H      CH.sub.3                                                                            H       CH                                   L-6   SC.sub.2 H.sub.5                                                                            H      OCH.sub.3                                                                           H       N                                    L-6   SC.sub.2 H.sub.5                                                                            H      OCH.sub.3                                                                           H       CH                                   L-6   SC.sub.2 H.sub.5                                                                            H      CH.sub.3                                                                            H       CH                                   L-6   SO.sub.2 C.sub.2 H.sub.5                                                                    H      CH.sub.3                                                                            H       CH                                   L-6   SO.sub.2 C.sub.2 H.sub.5                                                                    H      OCH.sub.3                                                                           H       N                                    L-6   SO.sub.2 C.sub.2 H.sub.5                                                                    H      OCH.sub.3                                                                           H       CH                                   L-6   S(CH.sub.2).sub.2 CH.sub.3                                                                  H      OCH.sub.3                                                                           H       N                                    L-6   SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H      OCH.sub.3                                                                           H       CH                                   L-6   SCH.sub.2 CH═CH.sub.2                                                                   H      OCH.sub.3                                                                           H       N                                    L-6   SO.sub.2 CH.sub.2 CH═CH.sub.2                                                           H      OCH.sub.3                                                                           H       CH                                   L-6   CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                             OCH.sub.3                                                                           H       CH                                   L-6   SO.sub.2 N(CH.sub.3).sub.2                                                                  CH.sub.3                                                                             OCH.sub.3                                                                           H       CH                                   L-6   SO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                             OCH.sub.3                                                                           H       CH                                   L-6   NO.sub.2      CH.sub.3                                                                             OCH.sub.3                                                                           H       CH                                   L-6   Cl            CH.sub.3                                                                             OCH.sub.3                                                                           H       CH                                   L-6   CH.sub.3      CH.sub.3                                                                             OCH.sub.3                                                                           H       CH                                   L-6   CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3                                                                           (CH.sub.2).sub.3 CH.sub.3                                                             CH                                   ______________________________________                                    

                  TABLE V                                                         ______________________________________                                        General Structure V                                                           R.sub.6     R       X        Y        Z                                       ______________________________________                                        Cl          H       OCH.sub.3                                                                              H        CH                                      NO.sub.2    H       OCH.sub.3                                                                              H        CH                                      NO.sub.2    H       OCH.sub.3                                                                              H        N                                       CO.sub.2 CH.sub.3                                                                         H       CH.sub.3 H        CH                                      CO.sub.2 CH.sub.3                                                                         H       OCH.sub.3                                                                              H        CH                                      CO.sub.2 CH.sub.3                                                                         H       OCH.sub.3                                                                              H        N                                       CO.sub.2 CH.sub.3                                                                         H       CH.sub.3 H        N                                       CO.sub.2 CH.sub.3                                                                         H       OCH.sub.3                                                                              CH.sub.3 CH                                      CO.sub.2 CH.sub.3                                                                         H       OCH.sub.3                                                                              C.sub.2 H.sub.5                                                                        CH                                      CO.sub.2 CH.sub.3                                                                         H       OCH.sub.3                                                                              (CH.sub.2).sub.3 CH.sub.3                                                              CH                                      CO.sub.2 C.sub.2 H.sub.5                                                                  H       CH.sub.3 H        CH                                      CO.sub.2 C.sub.2 H.sub.5                                                                  H       OCH.sub.3                                                                              H        CH                                      CO.sub.2 C.sub.2 H.sub.5                                                                  H       OCH.sub.3                                                                              H        N                                       SO.sub.2 N(CH.sub.3).sub.2                                                                H       CH.sub.3 H        CH                                      SO.sub.2 N(CH.sub.3).sub.2                                                                H       OCH.sub.3                                                                              H        N                                       SO.sub.2 N(CH.sub.3).sub.2                                                                H       OCH.sub.3                                                                              H        CH                                      OSO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              H        N                                       OSO.sub.2 CH.sub.3                                                                        H       CH.sub.3 H        CH                                      OSO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              H        CH                                      SO.sub.2 CH.sub.3                                                                         H       OCH.sub.3                                                                              H        N                                       SO.sub.2 CH.sub.3                                                                         H       OCH.sub.3                                                                              H        CH                                      SO.sub.2 CH.sub.3                                                                         H       CH.sub.3 H        CH                                      SO.sub.2 C.sub.2 H.sub.5                                                                  H       CH.sub.3 H        CH                                      SO.sub.2 C.sub.2 H.sub.5                                                                  H       OCH.sub.3                                                                              H        N                                       SO.sub.2 C.sub.2 H.sub.5                                                                  H       OCH.sub.3                                                                              H        CH                                      OCH.sub.3   H       OCH.sub.3                                                                              H        N                                       OCH.sub.3   H       CH.sub.3 H        CH                                      OCH.sub.3   H       OCH.sub.3                                                                              H        CH                                      OC.sub.2 H.sub.5                                                                          H       OCH.sub.3                                                                              H        CH                                      OC.sub.2 H.sub.5                                                                          H       CH.sub.3 H        CH                                      OC.sub.2 H.sub.5                                                                          H       OCH.sub.3                                                                              H        N                                       CO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3                                                                              H        CH                                      CO.sub.2 CH.sub.3                                                                         H       OCH.sub.3                                                                              (CH.sub.2).sub.3 CH.sub.3                                                              N                                       ______________________________________                                    

                                      TABLE VI                                    __________________________________________________________________________    General Structure VI                                                          R.sub.7                                                                          R.sub.8                                                                          Q.sub.1                                                                           R.sub.9                                                                          m R.sub.2                                                                          R  X   Y     Z  m.p. °C.                             __________________________________________________________________________    H  H  O   H  0 H  H  CH.sub.3                                                                          H     CH                                             H  H  O   H  0 H  H  OCH.sub.3                                                                         H     CH                                             H  H  O   H  0 H  H  OCH.sub.3                                                                         H     N                                              H  H  O   H  0 H  H  CH.sub.3                                                                          H     N                                              H  H  O   H  1 H  H  CH.sub.3                                                                          H     N                                              H  H  O   H  1 H  H  OCH.sub.3                                                                         H     N                                              H  H  O   H  1 H  H  OCH.sub.3                                                                         H     CH                                             H  H  O   CH.sub.3                                                                         0 H  H  CH.sub.3                                                                          H     CH                                             CH.sub.3                                                                         H  O   H  0 H  H  CH.sub.3                                                                          H     CH                                             CH.sub.3                                                                         H  O   H  0 H  H  CH.sub.3                                                                          H     N                                              CH.sub.3                                                                         H  O   H  0 H  H  OCH.sub.3                                                                         H     N                                              CH.sub.3                                                                         CH.sub.3                                                                         O   H  0 H  H  OCH.sub.3                                                                         H     N                                              CH.sub.3                                                                         CH.sub.3                                                                         O   H  0 H  H  OCH.sub.3                                                                         H     CH                                             C.sub.2 H.sub.5                                                                  H  O   H  0 H  H  CH.sub.3                                                                          H     CH                                             H  C.sub.2 H.sub.5                                                                  O   H  0 H  H  OCH.sub.3                                                                         H     N                                              CH.sub.3                                                                         H  O   H  1 H  H  OCH.sub.3                                                                         H     N                                              CH.sub.3                                                                         H  O   H  1 H  H  CH.sub.3                                                                          H     CH                                             CH.sub.3                                                                         H  O   H  1 H  H  OCH.sub.3                                                                         H     CH                                             C.sub.2 H.sub.5                                                                  H  O   H  1 H  H  OCH.sub.3                                                                         H     N                                              C.sub.2 H.sub.5                                                                  H  O   H  1 H  H  OCH.sub.3                                                                         H     CH                                             H  H  S   H  0 H  H  CH.sub.3                                                                          H     CH                                             H  H  S   H  0 H  H  OCH.sub.3                                                                         H     CH                                             H  H  S   H  0 H  H  OCH.sub.3                                                                         H     N                                              CH.sub.3                                                                         H  S   H  0 H  H  OCH.sub.3                                                                         H     N                                              CH.sub.3                                                                         H  S   H  0 H  H  OCH.sub.3                                                                         H     CH                                             CH.sub.3                                                                         H  S   H  0 H  H  CH.sub.3                                                                          H     CH                                             CH.sub.3                                                                         CH.sub.3                                                                         S   H  0 H  H  OCH.sub. 3                                                                        H     CH                                             H  C.sub.2 H.sub.5                                                                  S   H  0 H  H  OCH.sub.3                                                                         H     CH                                             H  C.sub.2 H.sub.5                                                                  S   H  0 H  H  OCH.sub.3                                                                         (CH.sub.2).sub.4 CH.sub.3                                                           CH                                             H  H  SO.sub.2                                                                          H  0 H  H  OCH.sub.3                                                                         H     N                                              H  H  SO.sub.2                                                                          H  0 H  H  CH.sub.3                                                                          H     CH                                             H  H  SO.sub.2                                                                          H  0 H  H  OCH.sub.3                                                                         H     CH                                             CH.sub.3                                                                         H  SO.sub.2                                                                          H  0 H  H  CH.sub.3                                                                          H     CH                                             CH.sub.3                                                                         H  SO.sub.2                                                                          H  0 H  H  OCH.sub.3                                                                         H     N                                              CH.sub.3                                                                         H  SO.sub.2                                                                          H  0 H  H  OCH.sub.3                                                                         H     CH                                             C.sub.2 H.sub.5                                                                  H  SO.sub.2                                                                          H  0 H  H  OCH.sub.3                                                                         H     N                                              C.sub.2 H.sub.5                                                                  H  SO.sub.2                                                                          H  0 H  H  OCH.sub.3                                                                         H     CH                                             C.sub.2 H.sub.5                                                                  H  SO.sub.2                                                                          H  0 H  H  CH.sub.3                                                                          H     CH                                             H  H  SO.sub.2                                                                          H  0 7-Cl                                                                             CH.sub.3                                                                         OCH.sub.3                                                                         H     CH                                             CH.sub.3                                                                         H  NH  H  1 H  H  OCH.sub.3                                                                         H     CH                                             CH.sub.3                                                                         H  NCH.sub.3                                                                         H  1 H  H  OCH.sub.3                                                                         H     CH                                             CH.sub.3                                                                         CH.sub.3                                                                         SO.sub.2                                                                          H  0 H  H  OCH.sub.3                                                                         H     N  149-150 (d)                                 H  H  SO.sub.2                                                                          H  0 H  H  OCH.sub.3                                                                         (CH.sub.2).sub.3 CH.sub.3                                                           CH                                             CH.sub.3                                                                         CH.sub.3                                                                         O   H  0 H  H  OCH.sub.3                                                                         (CH.sub.2).sub.4 CH.sub.3                                                           N                                              __________________________________________________________________________

                  TABLE VII                                                       ______________________________________                                        General Structure VII                                                         Q.sub.2                                                                            R.sub.10                                                                             R.sub.11                                                                              R.sub.2                                                                            R     X     Y        Z                               ______________________________________                                        O    H      H       H    H     CH.sub.3                                                                            H        CH                              O    H      H       H    H     OCH.sub.3                                                                           H        N                               O    H      H       H    H     CH.sub.3                                                                            H        CH                              O    H      H       H    H     OCH.sub.3                                                                           H        N                               O    CH.sub.3                                                                             H       H    H     CH.sub.3                                                                            H        CH                              O    CH.sub.3                                                                             H       H    H     OCH.sub.3                                                                           H        N                               O    CH.sub.3                                                                             H       H    H     OCH.sub.3                                                                           H        N                               O    CH.sub.3                                                                             CH.sub.3                                                                              H    H     OCH.sub.3                                                                           H        CH                              O    CH.sub.3                                                                             CH.sub.3                                                                              H    H     OCH.sub.3                                                                           H        N                               O    CH.sub.3                                                                             CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           H        N                               S    H      H       5-Cl H     CH.sub.3                                                                            H        CH                              S    H      H       H    H     OCH.sub.3                                                                           H        N                               S    H      H       H    H     OCH.sub.3                                                                           H        N                               S    CH.sub.3                                                                             H       H    H     OCH.sub.3                                                                           H        CH                              S    CH.sub.3                                                                             H       H    H     OCH.sub.3                                                                           H        N                               S    CH.sub.3                                                                             H       H    H     CH.sub.3                                                                            H        CH                              S    H      CH.sub.3                                                                              H    H     OCH.sub.3                                                                           H        N                               S    H      CH.sub.3                                                                              H    H     OCH.sub.3                                                                           H        CH                              S    H      H       H    H     OCH.sub.3                                                                           (CH.sub.2).sub.3 CH.sub.3                                                              CH                              ______________________________________                                    

                                      TABLE VIII                                  __________________________________________________________________________    General Structure VIII                                                        L   R  R.sub.2                                                                            R.sub.9                                                                          m  X     Y     Z  R.sub.23                                                                         R.sub.24                                  __________________________________________________________________________    L-11                                                                              H  H    H  0  CH.sub.3                                                                            H     CH                                              L-11                                                                              H  H    H  0  OCH.sub.3                                                                           H     N                                               L-11                                                                              H  H    H  0  OCH.sub.3                                                                           H     CH                                              L-11                                                                              H  H    H  0  CH.sub.3                                                                            H     N                                               L-11                                                                              H  H    H  0  OCH.sub.3                                                                           CH.sub.3                                                                            CH                                              L-11                                                                              H  H    H  0  OCH.sub.3                                                                           C.sub.2 H.sub.5                                                                     CH                                              L-11                                                                              H  H    H  0  OCH.sub.3                                                                           (CH.sub.2).sub.2 CH.sub.3                                                           CH                                              L-11                                                                              H  H    H  0  OCH.sub.3                                                                           (CH.sub.2).sub.3 CH.sub.3                                                           CH                                              L-11                                                                              H  H    H  1  CH.sub.3                                                                            H     N                                               L-11                                                                              H  H    H  1  OCH.sub.3                                                                           H     N                                               L-11                                                                              H  H    H  1  OCH.sub.3                                                                           H     CH                                              L-11                                                                              H  H    H  0  CH.sub.3                                                                            CH.sub.3                                                                            CH                                              L-11                                                                              H  H    H  0  OCH.sub.3                                                                           CH.sub.3                                                                            N                                               L-11                                                                              H  H    H  0  OCH.sub.2 CH.sub.3                                                                  CH.sub.3                                                                            CH                                              L-11                                                                              H   .sub.--m-Cl                                                                       H  0  CH.sub.3                                                                            H     CH                                              L-11                                                                              H   .sub.--m-Cl                                                                       H  0  OCH.sub.3                                                                           H     N                                               L-11                                                                              H   .sub.--m-Cl                                                                       H  0  OCH.sub.3                                                                           H     CH                                              L-11                                                                              H   .sub.--m-CF.sub.3                                                                 H  0  OCH.sub.3                                                                           H     N                                               L-11                                                                              H   .sub.--m-OCH.sub.3                                                                H  0  CH.sub.3                                                                            H     CH                                              L-11                                                                              H   .sub.--m-OCH.sub.3                                                                H  0  OCH.sub.3                                                                           H     N                                               L-11                                                                              H   .sub.--m-OCH.sub.3                                                                H  0  OCH.sub.3                                                                           H     CH                                              L-11                                                                              H   .sub.--m-F                                                                        H  1  OCH.sub.3                                                                           H     CH                                              L-11                                                                              H   .sub.--m-F                                                                        H  1  OCH.sub.3                                                                           H     N                                               L-11                                                                              H   .sub.-o-Br                                                                        H  1  OCH.sub.3                                                                           H     N                                               L-11                                                                              H  H    CH.sub.3                                                                         0  OCH.sub.3                                                                           H     CH                                              L-11                                                                              H  H    CH.sub.3                                                                         0  OCH.sub.3                                                                           H     N                                               L-11                                                                              CH.sub.3                                                                         H    H  0  OCH.sub.3                                                                           H     N                                               L-11                                                                              CH.sub.3                                                                         H    H  1  OCH.sub.3                                                                           H     CH                                              L-12*                                                                             H  H    CH.sub.3                                                                         0  OCH.sub.3                                                                           H     N                                               L-12                                                                              H  H    H  0  OCH.sub.3                                                                           H     CH                                              L-12                                                                              H  H    H  0  CH.sub.3                                                                            H     CH                                              L-12                                                                              H  H    H  1  OCH.sub.3                                                                           H     CH -- --                                        L-12                                                                              H  H    H  1  OCH.sub.3                                                                           H     N  -- --                                        L-12                                                                              H  H    H  1  CH.sub.3                                                                            H     CH -- --                                        L-12                                                                              H  H    H  0  OCH.sub.3                                                                           H     N  -- --                                        L-13                                                                              H  H    CH.sub.3                                                                         0  OCH.sub.3                                                                           H     CH H  H                                         L-13                                                                              H  H    H  0  CH.sub.3                                                                            H     CH H  H                                         L-13                                                                              H  H    H  0  OCH.sub.3                                                                           H     N  Cl Cl                                        L-13                                                                              H  H    H  0  OCH.sub.3                                                                           H     CH Cl Cl                                        L-13                                                                              H  H    H  1  CH.sub.3                                                                            H     CH Cl Cl                                        L-13                                                                              H  H    H  1  OCH.sub.3                                                                           H     N  H  H                                         L-13                                                                              H  H    H  1  OCH.sub.3                                                                           H     CH H  H                                         L-11                                                                              H  H    H  0  OCH.sub.3                                                                           (CH.sub.2).sub.3 CH.sub.3                                                           CH -- --                                        L-12                                                                              H  H    H  0  OCH.sub.3                                                                           (CH.sub.2).sub.3 CH.sub.3                                                           CH -- --                                        L-13                                                                              H  H    H  0  OCH.sub.3                                                                           (CH.sub.2).sub.3 CH.sub.3                                                           N  H  H                                         __________________________________________________________________________     *Q.sub.3 is S; otherwise Q.sub.3 is NCH.sub.3.                           

                  TABLE IX                                                        ______________________________________                                        General Structure IX                                                          R.sub.12     R.sub.2                                                                             R      X      Y       Z                                    ______________________________________                                        H            H     H      OCH.sub.3                                                                            H       CH                                   CH.sub.3     H     H      OCH.sub.3                                                                            H       CH                                   C.sub.2 H.sub.5                                                                            H     H      OCH.sub.3                                                                            H       CH                                   CH(CH.sub.3).sub.2                                                                         H     H      OCH.sub.3                                                                            H       CH                                   (CH.sub.2).sub.3 CH.sub.3                                                                  H     H      OCH.sub.3                                                                            H       CH                                   CH.sub.2 CH═CH.sub.2                                                                   H     H      OCH.sub.3                                                                            H       CH                                   CH.sub.2 CH.sub.2 OCH.sub.3                                                                H     H      OCH.sub.3                                                                            H       CH                                   CH.sub.2 CH(OCH.sub.3)CH.sub.3                                                             H     H      OCH.sub.3                                                                            H       CH                                   CH.sub.2 C.tbd.CH                                                                          H     H      OCH.sub.3                                                                            H       CH                                   CH.sub.2 C(CH.sub.3)═CH.sub.2                                                          H     H      OCH.sub.3                                                                            H       CH                                   CH.sub.2 C.sub.6 H.sub.5                                                                   H     H      OCH.sub.3                                                                            H       CH                                   CH.sub.2 CH.sub.2 F                                                                        H     H      OCH.sub.3                                                                            H       CH                                   CH.sub.2 CH.sub.2 Cl                                                                       H     H      OCH.sub.3                                                                            H       CH                                   CH.sub.3     H     H      OCH.sub.3                                                                            H       N                                    CH.sub.2 CH.sub.3                                                                          H     H      OCH.sub. 3                                                                           H       N                                    CH.sub.2 CH.sub.2 F                                                                        H     H      OCH.sub.3                                                                            H       N                                    CH.sub.2 CH.sub.2 OCH.sub.3                                                                H     H      OCH.sub.3                                                                            H       N                                    CH.sub.3     H     H      OCH.sub.3                                                                            (CH.sub.2).sub.3 CH.sub.3                                                             CH                                   ______________________________________                                    

                                      TABLE X                                     __________________________________________________________________________    General Structure X                                                           R.sub.12   R.sub.9                                                                          R  R.sub.2                                                                            m X     Y     Z                                         __________________________________________________________________________    H          H  H  H    0 CH.sub.3                                                                            H     CH                                        H          H  H  H    0 OCH.sub.3                                                                           H     CH                                        H          H  H  H    0 OCH.sub.3                                                                            .sub.--n-C.sub.4 H.sub.9                                                           N                                         H          H  H  H    0 OCH.sub.3                                                                           CH.sub.3                                                                            N                                         H          H  H  H    0 OCH.sub.3                                                                           C.sub.2 H.sub.5                                                                     CH                                        H          H  H  H    0 OCH.sub.3                                                                            .sub.--n-C.sub.3 H.sub.7                                                           CH                                        H          H  CH.sub.3                                                                         H    0 CH.sub.3                                                                            H     CH                                        H          CH.sub.3                                                                         H  H    0 OCH.sub.3                                                                           H     N                                         H          H  H  H    1 OCH.sub.3                                                                           H     CH                                        H          H  H  H    0 OCH.sub.3                                                                           H     N                                         CH.sub.3   H  H  H    0 CH.sub.3                                                                            H     N                                         CH.sub.3   H  H  H    0 OCH.sub.2 CH.sub.3                                                                  H     N                                         CH.sub.3   H  H  H    0 OCH.sub.3                                                                           H     CH                                        CH.sub.3   H  H  H    0 CH.sub.3                                                                            H     CH                                        C.sub.2 H.sub.5                                                                          H  H  H    0 OCH.sub.3                                                                           H     N                                         C.sub.2 H.sub.5                                                                          H  H  H    0 CH.sub.3                                                                            H     CH                                        C.sub.2 H.sub.5                                                                          H  H  H    0 OCH.sub.3                                                                           H     CH                                        CH(CH.sub.3).sub.2                                                                       H  H  H    0 CH.sub.3                                                                            H     CH                                        (CH.sub.2).sub.3 CH.sub.3                                                                H  H  H    0 OCH.sub.3                                                                           H     CH                                        (CH.sub.2).sub.2 CH(CH.sub.3).sub.2                                                      H  H  H    0 OCH.sub.3                                                                           H     CH                                        CH.sub.2 CF.sub.3                                                                        H  H  H    0 OCH.sub.3                                                                           H     N                                         (CH.sub.2).sub.3 Cl                                                                      H  H  H    0 OCH.sub.3                                                                           H     CH                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                              H  H  H    0 OCH.sub.3                                                                           H     CH                                        (CH.sub.2).sub.2 CH(OCH.sub.3)CH.sub.3                                                   H  H  H    0 OCH.sub.3                                                                           H     CH                                        CH.sub.2 CH═CH.sub.2                                                                 H  H  H    0 OCH.sub.3                                                                           H     CH                                        CH.sub.2 C(CH.sub.3)═CH.sub.2                                                        H  H  H    0 OCH.sub.3                                                                           H     CH                                        CH.sub.2 C.sub.6 H.sub.5                                                                 H  H  H    0 OCH.sub.3                                                                           H     CH                                        CH.sub.2 C.tbd.CH                                                                        H  H  H    0 OCH.sub.3                                                                           H     CH                                        CH.sub.2 C.tbd.CCH.sub.3                                                                 H  H  H    0 OCH.sub.3                                                                           H     CH                                        CH.sub.3   H  H  H    0 OCH.sub.3                                                                           (CH.sub.2).sub.4 CH.sub.3                                                           CH                                        CH.sub.2 CH.sub.2 F                                                                      H  H  H    0 OCH.sub.3                                                                           H     CH                                        CH.sub.2 CH.sub.2 F                                                                      H  H  H    0 OCH.sub.3                                                                           H     N                                         CH.sub.2 CH.sub.2 F                                                                      H  H  H    0 CH.sub.3                                                                            H     CH                                        CH.sub.2 CH.sub.2 Cl                                                                     H  H  H    0 OCH.sub.3                                                                           H     CH                                        CH.sub.2 CH.sub.2 Cl                                                                     H  H  7-Cl 0 CH.sub.3                                                                            H     CH                                        CH.sub.2 CH.sub.2 Cl                                                                     H  H  6-Cl 0 OCH.sub.3                                                                           H     CH                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                              H  H  H    0 OCH.sub.3                                                                           H     N                                         CH.sub.2 CH.sub.2 OCH.sub.3                                                              H  H  7-Cl 0 CH.sub.3                                                                            H     CH                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                              H  H  6-CH.sub.3                                                                         0 OCH.sub.3                                                                           H     CH                                        CH.sub.3   H  H  6-Cl 1 OCH.sub.3                                                                           H     CH                                        CH.sub.3   H  H  6-OCH.sub.3                                                                        0 OCH.sub.3                                                                           H     CH                                        CH.sub.3   H  H  6-CH.sub.3                                                                         0 OCH.sub.3                                                                           H     CH                                        CH.sub.3   H  H  6-OCF.sub.2 H                                                                      0 OCH.sub.3                                                                           H     CH                                        CH.sub.3   H  H  6-Cl 0 OCH.sub.3                                                                           H     CH                                        CH.sub.3   H  H  6-CF.sub.3                                                                         0 OCH.sub.3                                                                           H     CH                                        CH.sub.3   H  H  6-SCH.sub.3                                                                        0 OCH.sub.3                                                                           H     CH                                        CH.sub.3   H  H  6-Br 0 OCH.sub.3                                                                           H     CH                                        CH.sub.3   H  H  6-F  0 OCH.sub.3                                                                           H     CH                                        CF.sub.2 H H  H  H    0 OCH.sub.3                                                                           H     CH                                        CF.sub.2 H H  H  H    0 OCH.sub.3                                                                           H     N                                         CF.sub.2 H H  H  H    0 CH.sub.3                                                                            H     CH                                        CF.sub.2 H H  H  6-Cl 0 OCH.sub.3                                                                           H     CH                                        CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                                     H  H  H    0 OCH.sub.3                                                                           H     CH                                        CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                                     H  H  H    0 OCH.sub.3                                                                           H     N                                         CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                                     H  H  H    0 CH.sub.3                                                                            H     CH                                        CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                                     H  H  7-Cl 0 OCH.sub.3                                                                           H     CH                                        CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                                     H  H  6-Cl 0 OCH.sub.3                                                                           H     CH                                        CH.sub.2 CH═CH.sub.2                                                                 H  H  H    0 OCH.sub.3                                                                           H     N                                         CH.sub.2 CH═CH.sub.2                                                                 H  H  H    0 CH.sub.3                                                                            H     CH                                        CH.sub.2 CH═CH.sub.2                                                                 H  H  H    0 CH.sub.3                                                                            H     N                                         CH.sub.2 CH═CH.sub.2                                                                 H  H  7-Cl 0 OCH.sub.3                                                                           H     CH                                        CH.sub.2 CH═CH.sub.2                                                                 H  H  6-OCH.sub.3                                                                        0 OCH.sub.3                                                                           H     CH                                        __________________________________________________________________________

                                      TABLE XI                                    __________________________________________________________________________    General Structure XI                                                          L  R.sub.13                                                                             R.sub.14                                                                         R.sub.2                                                                            R  X      Y      Z                                          __________________________________________________________________________    L-15                                                                             H      -- H    H  CH.sub.3                                                                             H      CH                                         L-15                                                                             H      -- H    H  OCH.sub.3                                                                            H      CH                                         L-15                                                                             H      -- H    H  OCH.sub.3                                                                            H      N                                          L-15                                                                             CH.sub.3                                                                             -- H    H  CH.sub.3                                                                             H      CH                                         L-15                                                                             CH.sub.3                                                                             -- H    H  OCH.sub.3                                                                            H      CH                                         L-15                                                                             CH.sub.3                                                                             -- H    H  OCH.sub.3                                                                            H      N                                          L-15                                                                             C.sub.2 H.sub.5                                                                      -- H    H  CH.sub.3                                                                             H      CH                                         L-15                                                                             C.sub.2 H.sub.5                                                                      -- H    H  OCH.sub.3                                                                            H      N                                          L-15                                                                              .sub.--n-C.sub.3 H.sub.7                                                            -- H    H  OCH.sub.3                                                                            H      N                                          L-16                                                                             H      -- H    H  CH.sub.3                                                                             H      CH                                         L-16                                                                             H      -- H    H  OCH.sub.3                                                                            H      N                                          L-16                                                                             H      -- H    H  OCH.sub.3                                                                            H      CH                                         L-16                                                                             CH.sub.3                                                                             -- H    H  OCH.sub.3                                                                            H      N                                          L-16                                                                             CH.sub.3                                                                             -- H    H  OCH.sub.3                                                                            H      CH                                         L-16                                                                             CH.sub.3                                                                             -- H    H  CH.sub.3                                                                             H      CH                                         L-17                                                                             CH.sub.3                                                                             H  H    H  CH.sub.3                                                                             H      CH                                         L-17                                                                             CH.sub.3                                                                             H  H    H  OCH.sub.3                                                                            H      N                                          L-17                                                                             CH.sub.3                                                                             H  H    H  OCH.sub.3                                                                            H      CH                                         L-17                                                                             CH.sub.3                                                                             H  H    H  CH.sub.3                                                                             H      N                                          L-17                                                                             CH.sub.3                                                                             H  H    H  OCH.sub.3                                                                            CH.sub.3                                                                             CH                                         L-17                                                                             CH.sub.3                                                                             H  H    H  OCH.sub.3                                                                            C.sub.2 H.sub.5                                                                      CH                                         L-17                                                                             CH.sub.3                                                                             H  H    H  OCH.sub.3                                                                             .sub.--n-C.sub.3 H.sub.7                                                            CH                                         L-17                                                                             CH.sub.3                                                                             CH.sub.3                                                                         H    H  OCH.sub.3                                                                            H      N                                          L-17                                                                             CH.sub.3                                                                             CH.sub.3                                                                         H    H  OCH.sub.3                                                                            H      CH                                         L-17                                                                             CH.sub.3                                                                             CH.sub.3                                                                         H    H  CH.sub.3                                                                             H      CH                                         L-17                                                                             C.sub.2 H.sub.5                                                                      H  H    H  OCH.sub.3                                                                            H      N                                          L-17                                                                             C.sub.2 H.sub.5                                                                      H  H    H  OCH.sub.3                                                                            H      CH                                         L-17                                                                             C.sub.2 H.sub.5                                                                      H  H    H  CH.sub.3                                                                             H      CH                                         L-17                                                                             (CH.sub.2).sub.2 CH.sub.3                                                            H  H    H  OCH.sub.3                                                                            H      CH                                         L-17                                                                             CH.sub.3                                                                             H  H    CH.sub.3                                                                         OCH.sub.3                                                                            H      N                                          L-17                                                                             CH.sub.3                                                                             H  H    H  OCH.sub.2 CH.sub.3                                                                   H      CH                                         L-17                                                                             CH.sub.3                                                                             H  6-Cl H  OCH.sub.3                                                                            H      CH                                         L-17                                                                             CH.sub.3                                                                             H  6-CF.sub.3                                                                         H  OCH.sub.3                                                                            H      CH                                         L-17                                                                             CH.sub.3                                                                             H  6-Br H  OCH.sub.3                                                                            H      CH                                         L-17                                                                             CH.sub.3                                                                             H  6-F  H  OCH.sub.3                                                                            H      CH                                         L-17                                                                             CH.sub.3                                                                             H  6-CH.sub.3                                                                         H  OCH.sub.3                                                                            H      CH                                         L-17                                                                             CH.sub.3                                                                             H  6-OCH.sub.3                                                                        H  OCH.sub.3                                                                            H      CH                                         L-17                                                                             CH.sub.3                                                                             H  6-OCF.sub.2 H                                                                      H  OCH.sub.3                                                                            H      CH                                         L-17                                                                             CH.sub.3                                                                             H  6-SCH.sub.3                                                                        H  OCH.sub.3                                                                            H      CH                                         L-17                                                                             CH.sub.3                                                                             H  7-Cl H  OCH.sub.3                                                                            H      CH                                         L-17                                                                             CH.sub.3                                                                             H  6-Cl H  OCH.sub.3                                                                            H      N                                          L-17                                                                             CH.sub.3                                                                             H  H    H  OCH.sub.3                                                                            (CH.sub.2).sub.3 CH.sub.3                                                            CH                                         __________________________________________________________________________

                  TABLE XII                                                       ______________________________________                                        General Structure XII                                                         R.sub.13                                                                              R.sub.15       R      X     Y     Z                                   ______________________________________                                        H       Cl             H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              Cl             H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              Cl             H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              Cl             H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              CH.sub.3       H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              CH.sub.3       H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              CH.sub.3       H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              F              H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              Br             H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              Br             H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              Br             H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              NO.sub.2       H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              NO.sub.2       H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              NO.sub.2       H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                            H      CH.sub.3                                                                            H     N                                   CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                            H      CH.sub.3                                                                            H     CH                                  CH.sub. 3                                                                             CO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              CO.sub.2 C.sub.2 H.sub.5                                                                     H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              CO.sub.2 C.sub.2 H.sub.5                                                                     H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              CO.sub.2 C.sub.2 H.sub.5                                                                     H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                                   H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                                   H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                                   H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              SO.sub.2 CH.sub.3                                                                            H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              SO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              SO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              SO.sub.2 C.sub.2 H.sub.5                                                                     H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              SO.sub.2 C.sub.2 H.sub.5                                                                     H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              SO.sub.2 C.sub.2 H.sub.5                                                                     H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                           H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                           H      OCH.sub. 3                                                                          H     CH                                  CH.sub.3                                                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                           H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              SO.sub.2 CH.sub.2 CH═CH.sub.2                                                            H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              SO.sub.2 CH.sub.2 CH═CH.sub.2                                                            H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              SO.sub.2 CH.sub.2 CH═CH.sub.2                                                            H      OCH.sub.3                                                                           H     CH                                  C.sub.2 H.sub.5                                                                       CO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           H     CH                                  (CH.sub.2).sub.2 CH.sub.3                                                             CO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           (CH.sub.2).sub.4                                                                    CH                                                                      CH.sub.3                                  CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           (CH.sub.2).sub.3                                                                    N                                                                       CH.sub.3                                  CH.sub.3                                                                              CH.sub.2 CH.sub.2 CH.sub.3                                                                   H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              OCF.sub.2 H    H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              OCF.sub.2 H    H      OCH.sub.3                                                                           H     N                                   ______________________________________                                    

                  TABLE XIIA                                                      ______________________________________                                        General Structure XIIA                                                        R.sub.13                                                                              R.sub.15       R      X     Y     Z                                   ______________________________________                                        H       Cl             H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              Cl             H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              Cl             H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              Cl             H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              CH.sub.3       H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              CH.sub.3       H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              CH.sub.3       H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              F              H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              Br             H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              Br             H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              Br             H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              NO.sub.2       H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              NO.sub.2       H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              NO.sub.2       H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                            H      CH.sub.3                                                                            H     N                                   CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                            H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              CO.sub.2 C.sub.2 H.sub.5                                                                     H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              CO.sub.2 C.sub.2 H.sub.5                                                                     H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              CO.sub.2 C.sub.2 H.sub.5                                                                     H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                                   H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                                   H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                                   H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              SO.sub.2 CH.sub.3                                                                            H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              SO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              SO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              SO.sub.2 C.sub.2 H.sub.5                                                                     H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              SO.sub.2 C.sub.2 H.sub.5                                                                     H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              SO.sub.2 C.sub.2 H.sub.5                                                                     H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                           H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                           H      OCH.sub. 3                                                                          H     CH                                  CH.sub.3                                                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                           H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              SO.sub.2 CH.sub.2 CH═CH.sub.2                                                            H      CH.sub.3                                                                            H     CH                                  CH.sub.3                                                                              SO.sub.2 CH.sub.2 CH═CH.sub.2                                                            H      OCH.sub.3                                                                           H     N                                   CH.sub.3                                                                              SO.sub.2 CH.sub.2 CH═CH.sub.2                                                            H      OCH.sub.3                                                                           H     CH                                  C.sub.2 H.sub.5                                                                       CO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           H     CH                                  (CH.sub.2).sub.2 CH.sub.3                                                             CO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           (CH.sub.2).sub.3                                                                    N                                                                       CH.sub.3                                  CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           (CH.sub.2).sub.4                                                                    CH                                                                      CH.sub.3                                  CH.sub.3                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                                   H      OCH.sub.3                                                                           (CH.sub.2).sub.3                                                                    CH                                                                      CH.sub.3                                  CH.sub.3                                                                              CH.sub.2 CH.sub.3                                                                            H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              OCF.sub.2 H    H      OCH.sub.3                                                                           H     CH                                  CH.sub.3                                                                              OCF.sub.2 H    H      OCH.sub.3                                                                           H     N                                   ______________________________________                                    

                  TABLE XIIB                                                      ______________________________________                                        General Structure XIIB                                                        R.sub.13                                                                              R.sub.15      R      XY         Z                                     ______________________________________                                        H       Cl            H      CH.sub.3 H CH                                    CH.sub.3                                                                              Cl            H      CH.sub.3 H CH                                    CH.sub.3                                                                              Cl            H      OCH.sub.3 H                                                                              N                                     CH.sub.3                                                                              Cl            H      OCH.sub.3 H                                                                              CH                                    CH.sub.3                                                                              CH.sub.3      H      CH.sub.3 H CH                                    CH.sub.3                                                                              CH.sub.3      H      OCH.sub.3 H                                                                              CH                                    CH.sub.3                                                                              CH.sub.3      H      OCH.sub.3 H                                                                              N                                     CH.sub.3                                                                              F             H      OCH.sub.3 H                                                                              CH                                    CH.sub.3                                                                              Br            H      CH.sub.3 H CH                                    CH.sub.3                                                                              Br            H      OCH.sub.3 H                                                                              N                                     CH.sub.3                                                                              Br            H      OCH.sub.3 H                                                                              CH                                    CH.sub.3                                                                              NO.sub.2      H      CH.sub.3 H CH                                    CH.sub.3                                                                              NO.sub.2      H      OCH.sub.3 H                                                                              N                                     CH.sub.3                                                                              NO.sub.2      H      OCH.sub.3 H                                                                              CH                                    CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3 H                                                                              N                                     CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                           H      CH.sub.3 H N                                     CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                           H      CH.sub.3 H CH                                    CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3 H                                                                              CH                                    CH.sub.3                                                                              CO.sub.2 C.sub.2 H.sub.5                                                                    H      CH.sub.3 H CH                                    CH.sub.3                                                                              CO.sub.2 C.sub.2 H.sub.5                                                                    H      OCH.sub.3 H                                                                              CH                                    CH.sub.3                                                                              CO.sub.2 C.sub.2 H.sub.5                                                                    H      OCH.sub.3 H                                                                              N                                     CH.sub.3                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                                  H      CH.sub.3 H CH                                    CH.sub.3                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                                  H      OCH.sub.3 H                                                                              N                                     CH.sub.3                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                                  H      OCH.sub.3 H                                                                              CH                                    CH.sub.3                                                                              SO.sub.2 CH.sub.3                                                                           H      CH.sub.3 H CH                                    CH.sub.3                                                                              SO.sub.2 CH.sub.3                                                                           H      OCH.sub.3 H                                                                              CH                                    CH.sub.3                                                                              SO.sub.2 CH.sub.3                                                                           H      OCH.sub.3 H                                                                              N                                     CH.sub.3                                                                              SO.sub.2 C.sub.2 H.sub.5                                                                    H      CH.sub.3 H CH                                    CH.sub.3                                                                              SO.sub.2 C.sub.2 H.sub.5                                                                    H      OCH.sub.3 H                                                                              N                                     CH.sub.3                                                                              SO.sub.2 C.sub.2 H.sub.5                                                                    H      OCH.sub.3 H                                                                              CH                                    CH.sub.3                                                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H      CH.sub.3 H CH                                    CH.sub.3                                                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H      OCH.sub.3 H                                                                              CH                                    CH.sub.3                                                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H      OCH.sub.3 H                                                                              N                                     CH.sub.3                                                                              SO.sub.2 CH.sub.2 CH═CH.sub.2                                                           H      CH.sub.3 H CH                                    CH.sub.3                                                                              SO.sub.2 CH.sub.2 CH═CH.sub.2                                                           H      OCH.sub.3 H                                                                              N                                     CH.sub.3                                                                              SO.sub.2 CH.sub.2 CH═CH.sub.2                                                           H      OCH.sub.3 H                                                                              CH                                    C.sub.2 H.sub.5                                                                       CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3 H                                                                              CH                                    (CH.sub.2).sub.2 CH.sub.3                                                             CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3 H                                                                              CH                                    CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                             OCH.sub.3 H                                                                              CH                                    CH.sub.3                                                                              CO.sub.2 CH.sub.3                                                                           H      OCH.sub.3 (CH.sub.2).sub.4 CH.sub.3                                                      CH                                    ______________________________________                                    

                  TABLE XIII                                                      ______________________________________                                        General Structure XIII                                                        L    R.sub.13  R.sub.16  R   X      Y       Z                                 ______________________________________                                        L-19 H         --        H   CH.sub.3                                                                             H       CH                                L-19 H         --        H   OCH.sub.3                                                                            H       N                                 L-19 H         --        H   OCH.sub.3                                                                            H       CH                                L-19 CH.sub.3  --        H   CH.sub.3                                                                             H       CH                                L-19 CH.sub.3  --        H   OCH.sub.3                                                                            H       CH                                L-19 CH.sub.3  --        H   OCH.sub.3                                                                            H       N                                 L-19 C.sub.2 H.sub.5                                                                         --        H   OCH.sub.3                                                                            H       CH                                L-19 (CH.sub.2).sub.2 CH.sub.3                                                               --        H   OCH.sub.3                                                                            H       CH                                L-20 H         H         H   OCH.sub.3                                                                            H       CH                                L-20 H         CO.sub.2 CH.sub.3                                                                       H   OCH.sub.3                                                                            H       N                                 L-20 H         CO.sub.2 CH.sub.3                                                                       H   CH.sub.3                                                                             H       N                                 L-20 H         CO.sub.2 CH.sub.3                                                                       H   OCH.sub.3                                                                            H       CH                                L-20 H         CO.sub.2 CH.sub.3                                                                       H   CH.sub.3                                                                             H       CH                                L-20 H         CO.sub.2 C.sub.2 H.sub.5                                                                H   OCH.sub.3                                                                            H       CH                                L-20 H         CO.sub.2 C.sub.2 H.sub.5                                                                H   OCH.sub.3                                                                            H       N                                 L-20 H         CO.sub.2 C.sub.2 H.sub. 5                                                               H   CH.sub.3                                                                             H       CH                                L-20 H         SO.sub.2 CH.sub.3                                                                       H   CH.sub.3                                                                             H       CH                                L-20 H         SO.sub.2 CH.sub.3                                                                       H   OCH.sub.3                                                                            H       N                                 L-20 H         SO.sub.2 CH.sub.3                                                                       H   OCH.sub.3                                                                            H       CH                                L-20 H         SO.sub.2 C.sub.2 H.sub.5                                                                H   CH.sub.3                                                                             H       CH                                L-20 H         SO.sub.2 C.sub.2 H.sub.5                                                                H   OCH.sub.3                                                                            H       N                                 L-20 H         SO.sub.2 C.sub.2 H.sub.5                                                                H   OCH.sub.3                                                                            H       CH                                L-20 H         CO.sub.2 CH.sub.3                                                                       H   OCH.sub.3                                                                            (CH.sub.2).sub.3 CH.sub.3                                                             CH                                ______________________________________                                    

                                      TABLE XIV                                   __________________________________________________________________________    General Structure XIV                                                         L  R.sub.1  R.sub.2                                                                         R.sub.3                                                                             R.sub.4  R.sub.5                                                                              R.sub.6                                                                              X.sub.1                                                                          Y.sub.1                         __________________________________________________________________________    L-1                                                                              CO.sub.2 CH.sub.3                                                                      H --    --       --     --     H  O                               L-1                                                                              CO.sub.2 CH.sub.3                                                                      H --    --       --     --     CH.sub.3                                                                         O                               L-1                                                                              CO.sub.2 C.sub.2 H.sub.5                                                               H --    --       --     --     H  O                               L-1                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                             H --    --       --     --     H  O                               L-1                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                             H --    --       --     --     CH.sub.3                                                                         O                               L-1                                                                              OSO.sub.2 CH.sub.3                                                                     H --    --       --     --     H  O                               L-1                                                                              OSO.sub.2 CH.sub.3                                                                     H --    --       --     --     CH.sub.3                                                                         O                               L-1                                                                              OCF.sub.2 H                                                                            H --    --       --     --     H  O                               L-1                                                                              OCF.sub.2 H                                                                            H --    --       --     --     CH.sub.3                                                                         O                               L-1                                                                              OCH.sub.2 CH═CH.sub.2                                                              H --    --       --     --     H  O                               L-1                                                                              Q-1      H --    --       --     --     H  O                               L-1                                                                              CO.sub.2 CH.sub.3                                                                      H --    --       --     --     H  CH.sub.2                        L-1                                                                              CO.sub.2 Et                                                                            H --    --       --     --     H  CH.sub.2                        L-1                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                             H --    --       --     --     H  CH.sub.2                        L-1                                                                              OSO.sub.2 CH.sub.3                                                                     H --    --       --     --     H  CH.sub.2                        L-1                                                                              OCF.sub.2 H                                                                            H --    --       --     --     H  CH.sub.2                        L-2                                                                              --       --                                                                              Cl    --       --     --     H  O                               L-2                                                                              --       --                                                                              CH.sub.3                                                                            --       --     --     H  O                               L-2                                                                              --       --                                                                              OCH.sub.3                                                                           --       --     --     H  O                               L-2                                                                              --       --                                                                              SO.sub.2 CH.sub.3                                                                   --       --     --     H  O                               L-2                                                                              --       --                                                                              OSO.sub.2 CH.sub.3                                                                  --       --     --     H  O                               L-2                                                                              --       --                                                                              Cl    --       --     --     H  CH.sub.2                        L-2                                                                              --       --                                                                              SO.sub.2 CH.sub.3                                                                   --       --     --     H  CH.sub.2                        L-2                                                                              --       --                                                                              OCH.sub.3                                                                           --       --     --     H  CH.sub.2                        L-2                                                                              --       --                                                                              OSO.sub.2 CH.sub.3                                                                  --       --     --     H  CH.sub.2                        L-3                                                                              --       --                                                                              --    Cl       --     --     H  O                               L-3                                                                              --       --                                                                              --    CH.sub.3 --     --     H  O                               L-3                                                                              --       --                                                                              --    OCH.sub.3                                                                              --     --     H  O                               L-3                                                                              --       --                                                                              --    SO.sub.2 N(CH.sub.3).sub.2                                                             --     --     H  O                               L-3                                                                              --       --                                                                              --    SO.sub.2 CH.sub.3                                                                      --     --     H  O                               L-3                                                                              --       --                                                                              --    OCH.sub.2 CH═CH.sub.2                                                              --     --     H  O                               L-3                                                                              --       --                                                                              --    CH.sub.2 OCH.sub.3                                                                     --     --     H  O                               L-3                                                                              --       --                                                                              --    Cl       --     --     H  CH.sub.2                        L-3                                                                              --       --                                                                              --    OCH.sub.3                                                                              --     --     H  CH.sub.2                        L-3                                                                              --       --                                                                              --    SO.sub.2 N(CH.sub.3).sub.2                                                             --     --     H  CH.sub.2                        L-3                                                                              --       --                                                                              --    SO.sub.2 CH.sub.3                                                                      --     --     H  CH.sub.2                        L-4                                                                              --       --                                                                              --    --       CO.sub.2 CH.sub.3                                                                    --     H  O                               L-4                                                                              --       --                                                                              --    --       CO.sub.2 C.sub.2 H.sub.5                                                             --     H  O                               L-4                                                                              --       --                                                                              --    --       NO.sub.2                                                                             --     H  O                               L-4                                                                              --       --                                                                              --    --       Cl     --     H  O                               L-4                                                                              --       --                                                                              --    --       CH.sub.3                                                                             --     H  O                               L-4                                                                              --       --                                                                              --    --       SO.sub.2 N(CH.sub.3).sub.2                                                           --     H  O                               L-4                                                                              --       --                                                                              --    --       SO.sub.2 CH.sub.3                                                                    --     H  O                               L-4                                                                              --       --                                                                              --    --       CO.sub.2 CH.sub.3                                                                    --     H  CH.sub.2                        L-4                                                                              --       --                                                                              --    --       CO.sub.2 C.sub.2 H.sub.5                                                             --     H  CH.sub.2                        L-4                                                                              --       --                                                                              --    --       SO.sub. 2 CH.sub.3                                                                   --     H  CH.sub.2                        L-4                                                                              --       --                                                                              --    --       SO.sub.2 N(CH.sub.3).sub.2                                                           --     H  CH.sub.2                        L-4                                                                              --       --                                                                              --    --       NO.sub.2                                                                             --     H  CH.sub.2                        L-4                                                                              --       --                                                                              --    --       Cl     --     H  CH.sub.2                        L-5                                                                              --       --                                                                              --    --       CO.sub.2 CH.sub.3                                                                    --     H  O                               L-5                                                                              --       --                                                                              --    --       CO.sub.2 C.sub.2 H.sub.5                                                             --     H  O                               L-5                                                                              --       --                                                                              --    --       SO.sub.2 CH.sub.3                                                                    --     H  O                               L-5                                                                              --       --                                                                              --    --       SO.sub.2 N(CH.sub.3).sub.2                                                           --     H  O                               L-5                                                                              --       --                                                                              --    --       NO.sub.2                                                                             --     H  O                               L-5                                                                              --       --                                                                              --    --       Cl     --     H  O                               L-5                                                                              --       --                                                                              --    --       SO.sub.2 CH.sub.3                                                                    --     H  CH.sub.2                        L-5                                                                              --       --                                                                              --    --       CO.sub.2 CH.sub.3                                                                    --     H  CH.sub.2                        L-5                                                                              --       --                                                                              --    --       SO.sub.2 N(CH.sub.3).sub.2                                                           --     H  CH.sub.2                        L-5                                                                              --       --                                                                              --    --       NO.sub.2                                                                             --     H  CH.sub.2                        L-6                                                                              --       --                                                                              --    --       CO.sub.2 CH.sub.3                                                                    --     H  O                               L-6                                                                              --       --                                                                              --    --       Br     --     H  O                               L-6                                                                              --       --                                                                              --    --       SO.sub.2 CH.sub.3                                                                    --     H  O                               L-6                                                                              --       --                                                                              --    --       SO.sub.2 N(CH.sub.3).sub.2                                                           --     H  O                               L-6                                                                              --       --                                                                              --    --       CO.sub.2 CH.sub.3                                                                    --     H  CH.sub.2                        L-6                                                                              --       --                                                                              --    --       Br     --     H  CH.sub.2                        L-7                                                                              --       --                                                                              --    --       --     CO.sub.2 CH.sub.3                                                                    H  O                               L-7                                                                              --       --                                                                              --    --       --     CO.sub.2 C.sub.2 H.sub.5                                                             H  O                               L-7                                                                              --       --                                                                              --    --       --     SO.sub.2 CH.sub.3                                                                    H  O                               L-7                                                                              --       --                                                                              --    --       --     SO.sub.2 N(CH.sub.3                                                                  H.sub.2                                                                          O                               L-7                                                                              --       --                                                                              --    --       --     OCH.sub.3                                                                            H  O                               L-7                                                                              --       --                                                                              --    --       --     OSO.sub.2 CH.sub.3                                                                   H  O                               L-7                                                                              --       --                                                                              --    --       --     CO.sub.2 CH.sub.3                                                                    H  CH.sub.2                        L-7                                                                              --       --                                                                              --    --       --     SO.sub.2 CH.sub.3                                                                    H  CH.sub.2                        L-7                                                                              --       --                                                                              --    --       --     SO.sub.2 N(CH.sub.3).sub.2                                                           H  CH.sub.2                        L-7                                                                              --       --                                                                              --    --       --     OCH.sub.3                                                                            H  CH.sub.2                        L-7                                                                              --       --                                                                              --    --       --     CO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                         O                               __________________________________________________________________________

                                      TABLE XV                                    __________________________________________________________________________    General Structure XV                                                          L  R.sub.1  R.sub.2                                                                         R.sub.3                                                                             R.sub.4  R.sub.5                                                                              R.sub.6                                                                              X.sub.1                            __________________________________________________________________________    L-1                                                                              CO.sub.2 CH.sub.3                                                                      H --    --       --     --     H                                  L-1                                                                              CO.sub.2 CH.sub.3                                                                      H --    --       --     --     CH.sub.3                           L-1                                                                              CO.sub.2 C.sub.2 H.sub.5                                                               H --    --       --     --     H                                  L-1                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                             H --    --       --     --     H                                  L-1                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                             H --    --       --     --     CH.sub.3                           L-1                                                                              OSO.sub.2 CH.sub.3                                                                     H --    --       --     --     H                                  L-1                                                                              OSO.sub.2 CH.sub.3                                                                     H --    --       --     --     CH.sub.3                           L-1                                                                              OCF.sub.2 H                                                                            H --    --       --     --     H                                  L-1                                                                              OCF.sub.2 H                                                                            H --    --       --     --     CH.sub.3                           L-1                                                                              OCH.sub.2 CH═CH.sub.2                                                              H --    --       --     --     H                                  L-1                                                                              Q-1      H --    --       --     --     H                                  L-2                                                                              --       --                                                                              Cl    --       --     --     H                                  L-2                                                                              --       --                                                                              CH.sub.3                                                                            --       --     --     H                                  L-2                                                                              --       --                                                                              OCH.sub.3                                                                           --       --     --     H                                  L-2                                                                              --       --                                                                              SO.sub.2 CH.sub.3                                                                   --       --     --     H                                  L-2                                                                              --       --                                                                              OSO.sub.2 CH.sub.3                                                                  --       --     --     H                                  L-3                                                                              --       --                                                                              --    Cl       --     --     H                                  L-3                                                                              --       --                                                                              --    CH.sub.3 --     --     H                                  L-3                                                                              --       --                                                                              --    OCH.sub.3                                                                              --     --     H                                  L-3                                                                              --       --                                                                              --    SO.sub.2 N(CH.sub.3).sub.2                                                             --     --     H                                  L-3                                                                              --       --                                                                              --    SO.sub.2 CH.sub.3                                                                      --     --     H                                  L-3                                                                              --       --                                                                              --    OCH.sub.2 CH═CH.sub.2                                                              --     --     H                                  L-3                                                                              --       --                                                                              --    CH.sub.2 OCH.sub.3                                                                     --     --     H                                  L-4                                                                              --       --                                                                              --    --       CO.sub.2 CH.sub.3                                                                    --     H                                  L-4                                                                              --       --                                                                              --    --       CO.sub.2 C.sub.2 H.sub.5                                                             --     H                                  L-4                                                                              --       --                                                                              --    --       NO.sub.2                                                                             --     H                                  L-4                                                                              --       --                                                                              --    --       Cl     --     H                                  L-4                                                                              --       --                                                                              --    --       CH.sub.3                                                                             --     H                                  L-4                                                                              --       --                                                                              --    --       SO.sub.2 N(CH.sub.3).sub.2                                                           --     H                                  L-4                                                                              --       --                                                                              --    --       SO.sub.2 CH.sub.3                                                                    --     H                                  L-4                                                                              --       --                                                                              --    --       Cl     --     H                                  L-5                                                                              --       --                                                                              --    --       CO.sub.2 CH.sub.3                                                                    --     H                                  L-5                                                                              --       --                                                                              --    --       CO.sub.2 C.sub.2 H.sub.5                                                             --     H                                  L-5                                                                              --       --                                                                              --    --       SO.sub.2 CH.sub.3                                                                    --     H                                  L-5                                                                              --       --                                                                              --    --       SO.sub.2 N(CH.sub.3).sub.2                                                           --     H                                  L-5                                                                              --       --                                                                              --    --       NO.sub.2                                                                             --     H                                  L-5                                                                              --       --                                                                              --    --       Cl     --     H                                  L-6                                                                              --       --                                                                              --    --       CO.sub.2 CH.sub.3                                                                    --     H                                  L-6                                                                              --       --                                                                              --    --       Br     --     H                                  L-6                                                                              --       --                                                                              --    --       SO.sub.2 CH.sub.3                                                                    --     H                                  L-6                                                                              --       --                                                                              --    --       SO.sub.2 N(CH.sub.3).sub.2                                                           --     H                                  L-7                                                                              --       --                                                                              --    --       --     CO.sub.2 CH.sub.3                                                                    H                                  L-7                                                                              --       --                                                                              --    --       --     CO.sub.2 C.sub.2 H.sub.5                                                             H                                  L-7                                                                              --       --                                                                              --    --       --     SO.sub.2 CH.sub.3                                                                    H                                  L-7                                                                              --       --                                                                              --    --       --     SO.sub.2 N(CH.sub.3).sub.2                                                           H                                  L-7                                                                              --       --                                                                              --    --       --     OCH.sub.3                                                                            H                                  L-7                                                                              --       --                                                                              --    --       --     OSO.sub.3 CH.sub.3                                                                   H                                  __________________________________________________________________________

                                      TABLE XVI                                   __________________________________________________________________________    General Structure XVI                                                         L  R.sub.1  R.sub.2                                                                         R.sub.3                                                                             R.sub.4  R.sub.5                                                                              R.sub.6                                                                              X.sub.1                                                                          Y.sub.2                         __________________________________________________________________________    L-1                                                                              CO.sub.2 CH.sub.3                                                                      H --    --       --     --     H  H                               L-1                                                                              CO.sub.2 CH.sub.3                                                                      H --    --       --     --     CH.sub.3                                                                         H                               L-1                                                                              CO.sub.2 C.sub.2 H.sub.5                                                               H --    --       --     --     H  H                               L-1                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                             H --    --       --     --     H  H                               L-1                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                             H --    --       --     --     CH.sub.3                                                                         H                               L-1                                                                              OSO.sub.2 CH.sub.3                                                                     H --    --       --     --     H  H                               L-1                                                                              OSO.sub.2 CH.sub.3                                                                     H --    --       --     --     CH.sub.3                                                                         H                               L-1                                                                              OCF.sub.2 H                                                                            H --    --       --     --     H  H                               L-1                                                                              OCF.sub.2 H                                                                            H --    --       --     --     CH.sub.3                                                                         H                               L-1                                                                              OCH.sub.2 CH═ CH.sub.2                                                             H --    --       --     --     H  H                               L-1                                                                              Q-1      H --    --       --     --     H  H                               L-1                                                                              CO.sub.2 CH.sub.3                                                                      H --    --       --     --     H  CH.sub.3                        L-1                                                                              CO.sub.2 Et                                                                            H --    --       --     --     H  CH.sub.3                        L-1                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                             H --    --       --     --     H  CH.sub.3                        L-1                                                                              OSO.sub.2 CH.sub.3                                                                     H --    --       --     --     H  CH.sub.3                        L-1                                                                              OCF.sub.2 H                                                                            H --    --       --     --     H  CH.sub.3                        L-2                                                                              --       --                                                                              Cl    --       --     --     H  H                               L-2                                                                              --       --                                                                              CH.sub.3                                                                            --       --     --     H  H                               L-2                                                                              --       --                                                                              OCH.sub.3                                                                           --       --     --     H  H                               L-2                                                                              --       --                                                                              SO.sub.2 CH.sub.3                                                                   --       --     --     H  H                               L-2                                                                              --       --                                                                              OSO.sub.2 CH.sub.3                                                                  --       --     --     H  H                               L-2                                                                              --       --                                                                              Cl    --       --     --     H  CH.sub.3                        L-2                                                                              --       --                                                                              SO.sub.2 CH.sub.3                                                                   --       --     --     H  CH.sub.3                        L-2                                                                              --       --                                                                              OCH.sub.3                                                                           --       --     --     H  CH.sub.3                        L-2                                                                              --       --                                                                              OSO.sub.2 CH.sub.3                                                                  --       --     --     H  CH.sub.3                        L-3                                                                              --       --                                                                              --    Cl       --     --     H  H                               L-3                                                                              --       --                                                                              --    CH.sub.3 --     --     H  H                               L-3                                                                              --       --                                                                              --    OCH.sub.3                                                                              --     --     H  H                               L-3                                                                              --       --                                                                              --    SO.sub.2 N(CH.sub.3).sub.2                                                             --     --     H  H                               L-3                                                                              --       --                                                                              --    SO.sub.2 CH.sub.3                                                                      --     --     H  H                               L-3                                                                              --       --                                                                              --    OCH.sub.2 CH═CH.sub.2                                                              --     --     H  H                               L-3                                                                              --       --                                                                              --    CH.sub.2 OCH.sub.3                                                                     --     --     H  H                               L-3                                                                              --       --                                                                              --    Cl       --     --     H  CH.sub.3                        L-3                                                                              --       --                                                                              --    OCH.sub.3                                                                              --     --     H  CH.sub.3                        L-3                                                                              --       --                                                                              --    SO.sub.2 N(CH.sub.3).sub.2                                                             --     --     H  CH.sub.3                        L-3                                                                              --       --                                                                              --    SO.sub.2 CH.sub.3                                                                      --     --     H  CH.sub.3                        L-4                                                                              --       --                                                                              --    --       CO.sub.2 CH.sub.3                                                                    --     H  H                               L-4                                                                              --       --                                                                              --    --       CO.sub.2 C.sub.2 H.sub.5                                                             --     H  H                               L-4                                                                              --       --                                                                              --    --       NO.sub.2                                                                             --     H  H                               L-4                                                                              --       --                                                                              --    --       Cl     --     H  H                               L-4                                                                              --       --                                                                              --    --       CH.sub.3                                                                             --     H  H                               L-4                                                                              --       --                                                                              --    --       SO.sub.2 N(CH.sub.3).sub.2                                                           --     H  H                               L-4                                                                              --       --                                                                              --    --       SO.sub.2 CH.sub.3                                                                    --     H  H                               L-4                                                                              --       --                                                                              --    --       CO.sub.2 CH.sub.3                                                                    --     H  CH.sub.3                        L-4                                                                              --       --                                                                              --    --       CO.sub.2 C.sub.2 H.sub.5                                                             --     H  CH.sub.3                        L-4                                                                              --       --                                                                              --    --       SO.sub.2 CH.sub.3                                                                    --     H  CH.sub.3                        L-4                                                                              --       --                                                                              --    --       SO.sub.2 N(CH.sub.3).sub.2                                                           --     H  CH.sub.3                        L-4                                                                              --       --                                                                              --    --       NO.sub.2                                                                             --     H  CH.sub.3                        L-4                                                                              --       --                                                                              --    --       Cl     --     H  CH.sub.3                        L-5                                                                              --       --                                                                              --    --       CO.sub.2 CH.sub.3                                                                    --     H  H                               L-5                                                                              --       --                                                                              --    --       CO.sub.2 C.sub.2 H.sub.5                                                             --     H  H                               L-5                                                                              --       --                                                                              --    --       SO.sub.2 CH.sub.3                                                                    --     H  H                               L-5                                                                              --       --                                                                              --    --       SO.sub.2 N(CH.sub.3).sub.2                                                           --     H  H                               L-5                                                                              --       --                                                                              --    --       NO.sub.2                                                                             --     H  H                               L-5                                                                              --       --                                                                              --    --       Cl     --     H  H                               L-5                                                                              --       --                                                                              --    --       CO.sub.2 CH.sub.3                                                                    --     H  CH.sub.3                        L-5                                                                              --       --                                                                              --    --       SO.sub.2 CH.sub.3                                                                    --     H  CH.sub.3                        L-5                                                                              --       --                                                                              --    --       SO.sub.2 N(CH.sub.3).sub.2                                                           --     H  CH.sub.3                        L-5                                                                              --       --                                                                              --    --       NO.sub.2                                                                             --     H  CH.sub.3                        L-6                                                                              --       --                                                                              --    --       CO.sub.2 CH.sub.3                                                                    --     H  H                               L-6                                                                              --       --                                                                              --    --       Br     --     H  H                               L-6                                                                              --       --                                                                              --    --       SO.sub.2 CH.sub.3                                                                    --     H  H                               L-6                                                                              --       --                                                                              --    --       SO.sub.2 N(CH.sub.3).sub.2                                                           --     H  H                               L-6                                                                              --       --                                                                              --    --       CO.sub.2 CH.sub.3                                                                    --     H  CH.sub.3                        L-6                                                                              --       --                                                                              --    --       Br     --     H  CH.sub.3                        L-7                                                                              --       --                                                                              --    --       --     CO.sub.2 CH.sub.3                                                                    H  H                               L-7                                                                              --       --                                                                              --    --       --     CO.sub.2 C.sub.2 H.sub.5                                                             H  H                               L-7                                                                              --       --                                                                              --    --       --     SO.sub.2 CH.sub.3                                                                    H  H                               L-7                                                                              --       --                                                                              --    --       --     SO.sub.2 N(CH.sub.3).sub.2                                                           H  H                               L-7                                                                              --       --                                                                              --    --       --     OCH.sub.3                                                                            H  H                               L-7                                                                              --       --                                                                              --    --       --     OSO.sub.3 CH.sub.3                                                                   H  H                               L-7                                                                              --       --                                                                              --    --       --     CO.sub.2 CH.sub.3                                                                    H  CH.sub.3                        L-7                                                                              --       --                                                                              --    --       --     SO.sub.2 CH.sub.3                                                                    H  CH.sub.3                        L-7                                                                              --       --                                                                              --    --       --     SO.sub.2 N(CH.sub.3).sub.2                                                           H  CH.sub.3                        L-7                                                                              --       --                                                                              --    --       --     OCH.sub.3                                                                            H  CH.sub.3                        __________________________________________________________________________

                  TABLE XVII                                                      ______________________________________                                        General Structure XVII                                                        L                     X.sub.1                                                                              Y.sub.1                                          ______________________________________                                         ##STR42##            H      O                                                 ##STR43##            CH.sub.3                                                                             O                                                 ##STR44##            H      CH.sub.2                                          ##STR45##            H      O                                                 ##STR46##            H      O                                                 ##STR47##            H      O                                                 ##STR48##            H      O                                                 ##STR49##            H      O                                                 ##STR50##            H      O                                                 ##STR51##            H      O                                                 ##STR52##            H      O                                                 ##STR53##            H      O                                                 ##STR54##            H      O                                                 ##STR55##            H      O                                                 ##STR56##            H      O                                                ______________________________________                                    

                  TABLE XVIII                                                     ______________________________________                                        General Structure XVIII                                                       L                    X.sub.1                                                  ______________________________________                                         ##STR57##           H                                                         ##STR58##           H                                                         ##STR59##           H                                                         ##STR60##           H                                                         ##STR61##           H                                                         ##STR62##           CH.sub.3                                                  ##STR63##           H                                                         ##STR64##           H                                                         ##STR65##           H                                                         ##STR66##           H                                                         ##STR67##           H                                                         ##STR68##           H                                                         ##STR69##           CH.sub.3                                                  ##STR70##           H                                                         ##STR71##           H                                                        ______________________________________                                    

                  TABLE XIX                                                       ______________________________________                                        General Structure XIX                                                         L                     X.sub.1                                                                              Y.sub.2                                          ______________________________________                                         ##STR72##            H      H                                                 ##STR73##            H      H                                                 ##STR74##            H      H                                                 ##STR75##            H      CH.sub.3                                          ##STR76##            CH.sub.3                                                                             H                                                 ##STR77##            H      H                                                 ##STR78##            H      H                                                 ##STR79##            H      H                                                 ##STR80##            H      H                                                 ##STR81##            H      CH.sub.3                                          ##STR82##            H      H                                                 ##STR83##            H      H                                                 ##STR84##            H      CH.sub.3                                          ##STR85##            H      CH.sub.3                                          ##STR86##            H      CH.sub.3                                         ______________________________________                                    

                  TABLE XX                                                        ______________________________________                                        General Structure XX                                                          L                    X.sub.1                                                                              X.sub.2                                           ______________________________________                                         ##STR87##           H      CH.sub.3                                           ##STR88##           H      CH.sub.3                                           ##STR89##           H      CH.sub.3                                           ##STR90##           CH.sub.3                                                                             CH.sub.3                                           ##STR91##           H      C.sub.2 H.sub.5                                    ##STR92##           H      CH.sub.2 CF.sub.3                                  ##STR93##           H      CH.sub.3                                           ##STR94##           H      CH.sub.3                                           ##STR95##           H      CH.sub.2 CH.sub.3                                  ##STR96##           H      CH.sub.2 CF.sub.3                                  ##STR97##           H      CH.sub.3                                           ##STR98##           H      CH.sub.3                                           ##STR99##           H      CH.sub.3                                           ##STR100##          H      CH.sub.3                                           ##STR101##          H      CH.sub.3                                           ##STR102##          H      CH.sub.3                                           ##STR103##          H      CH.sub.3                                           ##STR104##          H      CH.sub.3                                           ##STR105##          H      CH.sub.3                                           ##STR106##          H      CH.sub.3                                           ##STR107##          H      CH.sub.3                                           ##STR108##          H      CH.sub.3                                           ##STR109##          H      CH.sub.3                                           ##STR110##          H      CH.sub.3                                          ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid inertdiluents(s). More specifically, they will contain these ingredients inthe following approximate proportions:

                  TABLE XXI                                                       ______________________________________                                                    Active  Weight Percent*                                                       Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             3-50     40-95     0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                        0.1-95      5-99.9  0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et. al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J., but other solids, either mined or manufactured, may beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York,1950. Solubility under 0.1% is preferred for suspension concentrates;solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia ofSurface Active Agents", Chemical Publishing Co., Inc., N.Y., 1964, listsurfactants and recommended uses. All formulations can contain minoramounts of additives to reduce foaming, caking, corrosion,microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon performed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc.,New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 4

Wettable Powder

    ______________________________________                                        2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                      80%                                              aminosulfonyl]benzoic acid, methyl ester                                      sodium alkylnaphthalenesulfonate                                                                           2%                                               sodium ligninsulfonate       2%                                               synthetic amorphous silica   3%                                               kaolinite                    13%                                              ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended and packaged.

EXAMPLE 5

Wettable Powder

    ______________________________________                                        2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                      50%                                              aminosulfonyl]benzoic acid, methyl ester                                      sodium alkylnaphthalenesulfonate                                                                            2%                                              low viscosity methyl cellulose                                                                              2%                                              diatomaceous earth           46%                                              ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 6

Granule

    ______________________________________                                        Wettable Powder of Example 5                                                                          5%                                                    attapulgite granules   95%                                                    (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                             ______________________________________                                    

A slurry of wettable powder containing 25% solids is sprayed on thesurface of attapulgite granules while tumbling in a double-cone blender.The granules are dried and packaged.

EXAMPLE 7

Extruded Pellet

    ______________________________________                                        2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                      25%                                              aminosulfonyl]benzoic acid, methyl ester                                      anhydrous sodium sulfate     10%                                              crude calcium ligninsulfonate                                                                               5%                                              sodium alkylnaphthalenesulfonate                                                                            1%                                              calcium/magnesium bentonite  59%                                              ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 8

Low Strength Granule

    ______________________________________                                        2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                      1%                                               aminosulfonyl]benzoic acid, methyl ester                                      N,N--dimethylformamide       9%                                               attapulgite granules         90%                                              (U.S.S. 20-40 sieve)                                                          ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 9

Aqueous Suspension

    ______________________________________                                        2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                      40%                                              aminosulfonyl]benzoic acid, methyl ester                                      polyacrylic acid thickener   0.3%                                             dodecylphenol polyethylene glycol ether                                                                    0.5%                                             disodium phosphate           1%                                               monosodium phosphate         0.5%                                             polyvinyl alcohol            1.0%                                             water                        56.7%                                            ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 10

Solution

    ______________________________________                                        2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                       5%                                              aminosulfonyl]benzoic acid, methyl ester, sodium salt                         water                        95%                                              ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 11

Oil Suspension

    ______________________________________                                        2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                      25%                                              aminosulfonyl]benzoic acid, methyl ester                                      polyoxyethylene sorbitol hexaoleate                                                                         5%                                              highly aliphatic hydrocarbon oil                                                                           70%                                              ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

EXAMPLE 12

Wettable Powder

    ______________________________________                                        2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                      20%                                              aminosulfonyl]benzoic acid, methyl ester                                      sodium alkylnaphthalenesulfonate                                                                           4%                                               sodium ligninsulfonate       4%                                               low viscosity methyl cellulose                                                                             3%                                               attapulgite                  69%                                              ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-millto produce particles essentially all below 100 microns, the material isreblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) andpackaged.

EXAMPLE 13

Low Strength Granule

    ______________________________________                                        2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                       0.1%                                            aminosulfonyl]benzoic acid, methyl ester                                      attapulgite granules         99.9%                                            (U.S.S. 20-40 mesh)                                                           ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double-cone blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and then packaged.

EXAMPLE 14

Granule

    ______________________________________                                        2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                      80%                                              aminosulfonyl]benzoic acid, methyl ester                                      wetting agent                 1%                                              crude ligninsulfonate salt (containing                                                                     10%                                              5-20% of the natural sugars)                                                  attapulgite clay              9%                                              ______________________________________                                    

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE 15

High Strength Concentrate

    ______________________________________                                        2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                       99%                                             aminosulfonyl]benzoic acid, methyl ester                                      silica aerogel               0.5%                                             synthetic amorphous silica   0.5%                                             ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 16

Wettable Powder

    ______________________________________                                        2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                       90%                                             aminosulfonyl]benzoic acid, methyl ester                                      dioctyl sodium sulfosuccinate                                                                              0.1%                                             synthetic fine silica        9.9%                                             ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 17

Wettable Powder

    ______________________________________                                        2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                      40%                                              aminosulfonyl]benzoic acid, methyl ester                                      sodium ligninsulfonate       20%                                              montmorillonite clay         40%                                              ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 18

Oil Suspension

    ______________________________________                                        2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                      35%                                              aminosulfonyl]benzoic acid, methyl ester                                      blend of polyalcohol carboxylic                                                                             6%                                              esters and oil soluble petroleum                                              sulfonates                                                                    xylene                       59%                                              ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 19

Dust

    ______________________________________                                        2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                      10%                                              aminosulfonyl]benzoic acid, methyl ester                                      attapulgite                  10%                                              Pyrophyllite                 80%                                              ______________________________________                                    

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

UTILITY

Test results indicate that the compounds of the present invention arehighly active preemergent or postermergent herbicides or plant growthregulants. Many of them have utility for broad-spectrum pre- and/orpost-emergence weed control in areas where complete control of allvegetation is desired, such as around fuel storage tanks, ammunitiondepots, industrial storage areas, parking lots, drive-in theaters,around billboards, highway and railroad structures. Alternatively, thesubject compounds are useful to modify plant growth.

The rates of application for the compounds of the invention aredetermined by a number of factors, including their use as plant growthmodifiers or as herbicides, the crop species involved, the types ofweeds to be controlled, weather and climate, formulations selected, modeof application, amount of foliage present, etc. In general terms, thesubject compounds should be applied at levels of around 0.01 to 5 kg/ha,the lower rates being suggested for use on lighter soils and/or thosehaving a low organic matter content, for selective weed control or forsituations where only short-term persistence is required.

The compounds of the invention may be used in combination with any othercommercial herbicide; examples of which are those of the triazine,triazole, uracil, urea, amide, diphenylether, carbamate and bipyridyliumtypes.

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures and results follow.

    __________________________________________________________________________    Compounds                                                                     __________________________________________________________________________    Compound 1                                                                             ##STR111##                                                           Compound 2                                                                             ##STR112##                                                           Compound 3                                                                             ##STR113##                                                           Compound 4                                                                             ##STR114##                                                           Compound 5                                                                             ##STR115##                                                           Compound 6                                                                             ##STR116##                                                           Compound 7                                                                             ##STR117##                                                           Compound 8                                                                             ##STR118##                                                           Compound 9                                                                             ##STR119##                                                           Compound 10                                                                            ##STR120##                                                           Compound 11                                                                            ##STR121##                                                           Compound 12                                                                            ##STR122##                                                           __________________________________________________________________________

TEST A

Seeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloacrusqalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia),morningglory (Ipomoea spp.), cocklebur (Xanthium pensylvanicum),sorghum, corn, soybean, sugarbeet, cotton, rice, wheat and purplenutsedge (Cyperus rotundus) tubers were planted and treatedpre-emergence with the test chemicals dissolved in a non-phytotoxicsolvent. At the same time, these crop and weed species were treated witha soil/foliage application. At the time of treatment, the plants rangedin height from 2 to 18 cm. Treated plants and controls were maintainedin a greenhouse for sixteen days, after which all species were comparedto controls and visually rated for response to treatment. The ratings,summarized in Table A, are based on a numerical scale extending from0=no injury, to 10=complete kill. The accompanying descriptive symbolshave the following meanings:

C=chlorosis or necrosis;

B=burn;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effects;

U=unusual pigmentation;

X=axillary stimulation;

S=albinism; and

6Y=abscised buds or flowers.

                                      TABLE A                                     __________________________________________________________________________            Cmpd. 1                                                                            Cmpd. 2                                                                            Cmpd. 3                                                                            Cmpd. 4                                                                            Cmpd. 5                                                                            Cmpd. 6                                                                            Cmpd. 7                                 Rate g/ha                                                                             50   50   50   50   50   50   0.05                                    __________________________________________________________________________    POST-EMERGENCE                                                                Morningglory                                                                          4C,8H                                                                              9C   3C,8H                                                                              9C   0    0    2C                                      Cocklebur                                                                             4C,8G                                                                              6C,9G                                                                              4C,9G                                                                              6C,9G                                                                              8G   0    2C,8G                                   Sicklepod                                                                             9C   --   --   --   --   --   2C                                      Nutsedge                                                                              3C,9G                                                                              0    2G   6C,9G                                                                              6G   0    8G                                      Crabgrass                                                                             4C,9G                                                                              0    2C,8G                                                                              0    5G   0    2C                                      Barnyardgrass                                                                         9C   0    4C,9H                                                                              4C,9H                                                                              3C,9H                                                                              0    3C,9H                                   Wild Oats                                                                             3C,9G                                                                              0    2G   4C,8G                                                                              3G   0    3C,5G                                   Wheat   4C,9G                                                                              0    2G   3C,8G                                                                              3G   0    3G                                      Corn    3C,9G                                                                              6C,9G                                                                              9C   9C   3C,9H                                                                              0    2C,9H                                   Soybean 4C,9G                                                                              5C,9G                                                                              4C,9G                                                                              3H,7G                                                                              2H,4G                                                                              0    2C,2H                                   Rice    9C   3C,9G                                                                              5C,9G                                                                              3C,8G                                                                              5C,9G                                                                              0    4C,9G                                   Sorghum 5C,9G                                                                              9C   9C   4C,9H                                                                              9G   0    2C,8H                                   Sugar beet                                                                            9C   9C   9C   3C,8G                                                                              5G   0    9C                                      Cotton  9C   3C,9G                                                                              3C,9G                                                                              9C   3C,8G                                                                              0    2C,8G                                   Velvetleaf                            --                                      Cheatgrass                            --                                      PRE-EMERGENCE                                                                 Morningglory                                                                          8H   3C,9G                                                                              8G   9G   5G    0   3G                                      Cocklebur                                                                             6H   7G   7H   3C,8G                                                                              8G   --   4G                                      Sicklepod                                                                             6G   --   --   --   --   --   0                                       Nutsedge                                                                              2C,8G                                                                              0    0    3C,5G                                                                              0    0    0                                       Crabgrass                                                                             2G   0    0    0    0    0    0                                       Barnyardgrass                                                                         9H   0    4C,4H                                                                              3C,7H                                                                              2G   0    1H                                      Wild Oats                                                                             4C,9G                                                                              0    2G   5G   8G   0    5G                                      Wheat   5C,9H                                                                              0    0    2G   6G   2G   5G                                      Corn    9G   5G   2C,8G                                                                              5G   8H   2C   9G                                      Soybean 2C,8G                                                                              2C,8G                                                                              4C,6G                                                                              3G   2C,5G                                                                              0    5G                                      Rice    10E  8G   2C,5G                                                                              3C,8G                                                                              4C,9H                                                                              2C   5G                                      Sorghum 9H   2C,8H                                                                              2C,9G                                                                              3C,7G                                                                              3C,7G                                                                              2C   2C,9G                                   Sugar beet                                                                            3C,9G                                                                              9C   4C,8G                                                                              9G   8H   0    4G                                      Cotton  8G   9G   5G   8G   5G   0    6G                                      Velvetleaf                            --                                      Cheatgrass                            --                                      __________________________________________________________________________            Cmpd. 8                                                                             Cmpd. 9                                                                             Cmpd. 10                                                                            Cmpd. 11                                                                            Compound 12                                   Rate g/ha                                                                             0.05  0.05  0.05  0.05  0.4  0.05                                     __________________________________________________________________________    POST-EMERGENCE                                                                Morningglory                                                                          2C,5G 4G    5G    0     10C  10C                                      Cocklebur                                                                             2C,8H 9C    2C,9H 4C,9H 9C   10C                                      Sicklepod                                                                             --    --    --    --    --   --                                       Nutsedge                                                                              2C,9G 3C,8G 0     2C,9G 10C  9C                                       Crabgrass                                                                             0     2C,5G 0     0     4C,8G                                                                              5G                                       Barnyardgrass                                                                         3C,9H 3C,8H 2C,6H 4C,8H 9C   4C,9H                                    Wild Oats                                                                             --    4C,8G 0     3G    3C,9G                                                                              0                                        Wheat   2C,6G 2C,7G 0     3G    8G   0                                        Corn    2C,9G 3C,9H 0     3C,9H 9C   3C,8H                                    Soybean 2C,7H 3C,6H 2C,4H 4H    5C,9G                                                                              3C,9G,7X                                 Rice    5C,9G 4C,9H 4C,9G 4C,9G 9C   6C,9G                                    Sorghum 9G    4C,9G 4C,9H 4C,9G 9C   6C,9H                                    Sugar beet                                                                            0     9C    10C   9C    9C   5C,9G                                    Cotton  5C,9G 2C,8G 4C,9G 5G    9C   9C                                       Velvetleaf                                                                            2C,9G 3C,9G 2C,5G 4C,9G 9C   10C                                      Cheatgrass                                                                            2C,5G 2C,5G 0     5G    9C   6C,9G                                    PRE-EMERGENCE                                                                 Morningglory                                                                          3G    7G    2C,2H 4G    10C  10C                                      Cocklebur                                                                             --    9H    3C,8H 8G    9H   --                                       Sicklepod                                                                             --    --    --    --    --   --                                       Nutsedge                                                                              6G    6G    0     5G    10E  10E                                      Crabgrass                                                                             0     5G    0     0     2C,5G                                                                              4C,7G                                    Barnyardgrass                                                                         3C,9H 4C,9H 3C,8H 2C,5H 5C,9H                                                                              5C,8H                                    Wild Oats                                                                             6G    2C,8G 3C,8G 6G    4C,9G                                                                              4C,8G                                    Wheat   6G    9G    2C,7G 4G    3C,9H                                                                              7G                                       Corn    2C,7G 2C,8G 3C,7G 2C,6G 3C,8H                                                                              3C,8G                                    Soybean 0     2C,5G 2C    2C    3C,8H                                                                              2C,6H                                    Rice    5C,9G 9H    3C,8G 5C,9H 10E  3C,9H                                    Sorghum 2C,9G 9H    3C,7G 2C,9H 7C,9H                                                                              3C,8G                                    Sugar beet                                                                            8G    9G    9C    5C,9G 6C,9G                                                                              9C                                       Cotton  2G    7G    2C    2C,4G 6C,9G                                                                              9G                                       Velvetleaf                                                                            8G    9G    8G    9G    9C   5C,9G                                    Cheatgrass                                                                            7G    8G    2C,8G 3C,8G 10E  4C,9H                                    __________________________________________________________________________

What is claimed is:
 1. A compound of the formula ##STR123## andagriculturally suitable salts thereof, whereinW₁ is O or S; R is H orCH₃ ; L is ##STR124## R₁ is OCH₂ CH₂ OCH₃, CO₂ R₁₇, SO₂ NR₁₈ R₁₉, SO₂N(OCH₃)CH₃, OSO₂ R₂₀, WCF₃, WCHF₂, C₃ -C₄ alkenyloxy, C₃ -C₄ alkynyloxy,C₁ -C₂ alkyl substituted with OCH₃ or OCH₂ CH₃, C₆ H₅, C₃ -C₄ alkynyl,CH═CHCF₃, CH═CHBr, or Q; q is ##STR125## R₂ is H, F, Cl, Br, CF₃, C₁ -C₂alkyl, C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, C₂ -C₃ alkoxyalkyl, C₂ -C₃alkylthioalkyl or OCF₂ H; R₃ is H, CH₃, OCH₃, F, Cl, Br, SO₂ N(CH₃)₂,OSO₂ CH₃ or S(O)_(n) CH₃ ; R₄ is CH₃, CH₂ CH₃, OCH₃, OCH₂ CH₃, F, Cl,Br, SO₂ NR₁₈ R₁₉, SO₂ N(OCH₃)CH₃, S(O)_(n) R₂₁, C₃ -C₄ alkenyloxy, CH₂OCH₃ or CH₂ OCH₂ CH₃ ; R₅ is F, Cl, Br, NO₂, CO₂ R₁₇, SO₂ NR₁₈ R₁₉, SO₂N(OCH₃)CH₃ or S(O)_(n) R₂₁ ; R₆ is Cl, NO₂, CO₂ CH₃, CO₂ CH₂ CH₃, SO₂N(CH₃)₂, OSO₂ CH₃, SO₂ CH₃, SO₂ CH₂ CH₃, OCH₃ or OCH₂ CH₃ ; R₇ is H, CH₃or CH₂ CH₃ ; R₈ is H, CH₃ or CH₂ CH₃ ; R₉ is H or CH₃ ; R₁₀ is H or CH₃; R₁₁ is H or CH₃ ; R₁₂ is H, C₁ -C₅ alkyl, C₂ -C₃ alkoxycarbonyl, C₂-C₃ alkylcarbonyl, C₁ -C₃ alkyl substituted by 1-3 halogens selectedfrom 0-3 F, 0-3 Cl or 0-1 Br, C₂ -C₄ alkyl substituted by OCH₃, C₃ -C₄alkenyl, C₃ -C₄ alkynyl or benzyl; R₁₃ is H or C₁ -C₃ alkyl; R₁₄ is H orCH₃ ; R₁₅ is C₁ -C₃ alkyl, F, Cl, Br, NO₂, CO₂ R₁₇, SO₂ NR₁₈ R₁₉, SO₂R₂₁ or OCF₂ H; R₁₆ is H, CO₂ CH₃, CO₂ CH₂ CH₃, SO₂ CH₃ or SO₂ CH₂ CH₃ ;R₁₇ is C₁ -C₄ alkyl, CH₂ CH₂ OCH₃, CH₂ CH₂ Cl or CH₂ CH═CH₂ ; R₁₈ is Hor C₁ -C₃ alkyl; R₁₉ is C₁ -C₃ alkyl; R₂₀ is C₁ -C₃ alkyl or N(CH₃)₂ ;R₂₁ is C₁ -C₃ alkyl or CH₂ CH═CH₂ ; R₂₂ is H or C₁ -C₃ alkyl; R₂₃ is Hor Cl; R₂₄ is H or Cl; R₂₅ is H or CH₃ ; m is 0 or 1; n is 0 or 2; Q₁ isO, S, SO₂ or NR₁₄ ; Q₂ is O or S; Q₃ is S or NR₂₂ ; W is O, S or SO₂ ; Ais ##STR126## X is H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkyl, C₁-C₃ haloalkoxy, C₂ -C₄ alkoxyalkoxy, C₁ -C₃ alkylamino, di(C₁ -C₂alkyl)amino, amino or cyclopropyl; Y is H, C₁ -C₅ alkyl, Br, I, phenyloptionally substituted with CH₃, OCH₃, halogen, NO₂, CF₃ or SCH₃, or C₁-C₃ alkyl substituted with OH, OCH₃, OC₂ H₅ or F; and Z is CH;providedthat (i) the total number of carbon atoms of R₁₈ and R₁₉ is less than orequal to four; (ii) when m is 1, then R₉ is H; (iii) when L is L-17,then R₁₃ and R₁₄ are not simultaneously H; (iv) when L is L-18, then R₁₅is adjacent to the sulfonylurea bridge SO₂ NHC(W₁)N(R)A; (v) when L isL-8 and Q₁ is NR₁₄, then m is 1; (vi) when the total number of carbonatoms of X and Y is greater than four, then the combined number ofcarbons of the substituents on L is less than or equal to four; and(vii) when L is L-8, L-9, L-11, L-12 or L-17 and R₂ is C₂ -C₃alkoxyalkyl or C₂ -C₃ alkylthioalkyl, then Y is other than H or C₁ -C₂alkyl.
 2. Compounds of claim 1 where R is H and W₁ is O.
 3. Compounds ofclaim 2 where Y is H or C₁ -C₃ alkyl.
 4. Compounds of claim 3 where L isL-1, L-2, L-3, L-4, L-5, L-6, L-8, L-9, L-10, L-11, L-12, L-13, L-17 orL-18, Q₁ is O, S or SO₂ and X is CH₃, CH₂ CH₃, OCH₃, OCH₂ CH₃, CH₂ OCH₃,CH₂ OCH₂ CH₃, OCH₂ CF₃, OCH₂ CF₂ H, OCH₂ CH₂ F or OCF₂ H.
 5. Compoundsof claim 4 where R₁ is CO₂ R₁₇, SO₂ NR₁₈ R₁₉, SO₂ N(OCH₃)CH₃, WCF₃,WCHF₂, ##STR127## R₂ is H, F, Cl, CH₃, OCH₃ or SCH₃ ; R₃ is CH₃, OCH₃,Cl, Br, OSO₂ CH₃ or S(O)_(n) CH₃ ;R₄ is CH₃, OCH₃, Cl, SO₂ N(CH₃)₂, SO₂CH₃ or SO₂ CH₂ CH₃ ; R₅ is Cl, NO₂, CO₂ R₁₇, SO₂ N(CH₃)₂, SO₂ CH₃ or SO₂CH₂ CH₃ ; R₇ is H or CH₃ ; R₈ is H or CH₃ ; R₉ is H; R₁₁ is H; R₁₂ is H,C₁ -C₄ alkyl, CH₂ CH₂ OCH₃ or CH₂ CH═CH₂ ; R₁₃ is H or CH₃ ;R₁₅ is CH₃,CH₂ CH₃, Cl, NO₂, CO₂ CH₃, CO₂ CH₂ CH₃, Br, SO₂ N(CH₃)₂, SO₂ CH₃, SO₂CH₂ CH₃ or OCF₂ H; R₁₈ is H or CH₃ ; R₁₉ is C₁ -C₂ alkyl; and W is O orS.
 6. Compounds of claim 5 where X is CH₃, CH₂ CH₃, OCH₃ or OCH₂ CH₃ andY is H or CH₃.
 7. Compounds of claim 6 where L is L-1 and R₁ is CO₂ CH₃,CO₂ CH₂ CH₃, SO₂ N(CH₃)₂, or OCF₂ H.
 8. Compounds of claim 6 where L isL-2.
 9. Compounds of claim 6 where L is L-4.
 10. Compounds of claim 6where L is L-5.
 11. Compounds of claim 6 where L is L-8.
 12. Compoundsof claim 6 where L is L-9.
 13. Compounds of claim 6 where L is L-10. 14.Compounds of claim 6 where L is L-11.
 15. Compounds of claim 6 where Lis L-12.
 16. Compounds of claim 6 where L is L-13.
 17. Compounds ofclaim 6 where L is L-17.
 18. Compounds of claim 6 where L is L-18. 19.The compound of claim 1 that is2-[[(4-ethynyl-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoicacid, methyl ester.
 20. A composition for the control of undesirablevegetation consisting essentially of a compound of claim 1 and at leastone of (a) a surface active agent, and (b) a solid or liquid diluent.21. A composition for the control of undesirable vegetation consistingessentially of a compound of claim 2 and at least one of (a) a surfaceactive agent, and (b) a solid or liquid diluent.
 22. A composition forthe control of undesirable vegetation consisting essentially of acompound of claim 3 and at least one of (a) a surface active agent, and(b) a solid or liquid diluent.
 23. A composition for the control ofundesirable vegetation consisting essentially of a compound of claim 4and at least one of (a) a surface active agent, and (b) a solid orliquid diluent.
 24. A composition for the control of undesirablevegetation consisting essentially of a compound of claim 5 and at leastone of (a) a surface active agent, and (b) a solid or liquid diluent.25. A composition for the control of undesirable vegetation consistingessentially of a compound of claim 6 and at least one of (a) a surfaceactive agent, and (b) a solid or liquid diluent.
 26. A composition forthe control of undesirable vegetation consisting essentially of acompound of claim 7 and at least one of (a) a surface active agent, and(b) a solid or liquid diluent.
 27. A composition for the control ofundesirable vegetation consisting essentially of a compound of claim 8and at least one of (a) a surface active agent, and (b) a solid orliquid diluent.
 28. A composition for the control of undesirablevegetation consisting essentially of a compound of claim 9 and at leastone of (a) a surface active agent, and (b) a solid or liquid diluent.29. A method for the control of undesirable vegetation comprisingapplying to the locus of such vegetation an herbicidally effectiveamount of a compound of claim
 1. 30. A method for the control ofundesirable vegetation comprising applying to the locus of suchvegetation an herbicidally effective amount of a compound of claim 2.31. A method for the control of undesirable vegetation comprisingapplying to the locus of such vegetation an herbicidally effectiveamount of a compound of claim
 3. 32. A method for the control ofundesirable vegetation comprising applying to the locus of suchvegetation an herbicidally effective amount of a compound of claim 4.33. A method for the control of undesirable vegetation comprisingapplying to the locus of such vegetation an herbicidally effectiveamount of a compound of claim
 5. 34. A method for the control ofundesirable vegetation comprising applying to the locus of suchvegetation an herbicidally effective amount of a compound of claim 6.35. A method for the control of undesirable vegetation comprisingapplying to the locus of such vegetation an herbicidally effectiveamount of a compound of claim
 7. 36. A method for the control ofundesirable vegetation comprising applying to the locus of suchvegetation an herbicidally effective amount of a compound of claim 8.37. A method for the control of undesirable vegetation comprisingapplying to the locus of such vegetation an herbicidally effectiveamount of a compound of claim
 9. 38. A compound according to claim 1wherein L is selected from the group L-1, L-2, L-3 and L-5 through L-20.39. Compounds of claim 6 where L is L-3.
 40. Compounds of claim 6 whereL is L-6.
 41. Compounds of claim 6 where L is L-7.
 42. Compounds ofclaim 6 where L is L-14.
 43. Compounds of claim 6 where L is L-15. 44.Compounds of claim 6 where L is L-16.
 45. Compounds of claim 6 where Lis L-19.
 46. Compounds of claim 6 where L is L-20.
 47. A compoundaccording to claim 1 wherein when L is L-4, R₅ is selected from F, Cl,Br, NO₂, CO₂ R₁₇, SO₂ NR₁₈ R₁₉, SO₂ N(OCH₃)CH₃ and S(O)_(n) R₂₁.
 48. Acompound according to claim 3: ##STR128##